While many flock to ski towns for the thrill of carving down snow-covered slopes, there’s a growing trend of families seeking the enchantment of winter wonderlands without strapping on skis. These travelers are drawn to the cozy ambiance, stunning landscapes, and diverse activities that ski towns offer beyond the ski lifts.

From horse-drawn sleigh rides through snowy forests to ice skating under twinkling lights, these destinations provide a magical winter experience for all.

Join us as we explore some of the best ski towns in the USA, where families can create unforgettable memories without ever setting foot on a ski run.

1. Park City, Utah

Park City’s silver mining history and modern amenities make it a captivating destination for families. Take a stroll down Historic Main Street, which is lined with colorful buildings, housing shops, restaurants, and galleries. The Utah Olympic Park, built for the 2002 Winter Olympics, offers thrilling activities like bobsledding and ski jumping into airbags.

Families can also enjoy snowshoeing, cross-country skiing, or a magical horse-drawn sleigh ride. For a unique experience, visit the Homestead Crater, a geothermal spring hidden within a 55-foot tall, beehive-shaped limestone rock, where you can soak in the warm waters or even try paddleboard yoga.

3. Stowe, Vermont

Stowe may be renowned for its skiing, but it offers plenty for non-skiers too. This picturesque New England town boasts the charm of a Norman Rockwell painting come to life. Families can enjoy a scenic gondola ride to the top of Mount Mansfield for breathtaking views, or explore the quaint downtown filled with boutiques and art galleries.

The Vermont Ski and Snowboard Museum looks at winter sports history. For outdoor adventures, try dog sledding, ice fishing, or snowmobiling through the snowy forests. End your day with a tour and tasting at the well-known Ben & Jerry’s Ice Cream Factory, just a short drive away in Waterbury.

4. Leavenworth, Washington

Nestled in the Cascade Mountains, Leavenworth is a Bavarian-styled village that transforms into a winter wonderland annually. Families can enjoy the town’s famous Christmas Lighting Festival, where over half a million lights illuminate the snow-covered streets.

Take a scenic horse-drawn sleigh ride through the snowy countryside, go tubing at Leavenworth Ski Hill, or try your hand at snowshoeing in the nearby national forest. The Nutcracker Museum offers a unique indoor experience, while the local shops and eateries serving German-inspired cuisine add to the charm. Don’t miss the opportunity to sip hot cocoa while watching ice carvers create intricate sculptures during the annual IceFest in January.

5. Lake Placid, New York

Lake Placid, nestled in the Adirondack Mountains, offers a perfect blend of Olympic history and small-town charm. Families can tour the Olympic Museum and take an exhilarating bobsled ride at the Olympic Sports Complex. For a more relaxed experience, enjoy ice skating on Mirror Lake or take a scenic gondola ride up Whiteface Mountain.

The Wild Center, a natural history museum, features indoor and outdoor exhibits, including the Wild Walk – an elevated trail through the treetops. In the evenings, cozy up by a fire in one of the many rustic lodges or enjoy s’mores under the stars at a local resort.

6. Mammoth Lakes, California

Mammoth Lakes offers a stunning Sierra Nevada backdrop for winter adventures. Families can explore the frozen lakes and waterfalls of the Lakes Basin on snowshoes or cross-country skis. Take a thrilling snowmobile tour through Inyo National Forest or soak in the natural hot springs at Wild Willy’s. The Mammoth Ice Rink provides picturesque outdoor skating with mountain views.

For a unique experience, visit the Mammoth Rock ‘N’ Bowl for bowling, golf simulators, and foosball. Don’t miss the chance to take a scenic gondola ride to the summit of Mammoth Mountain for breathtaking panoramic views of the surrounding peaks and valleys.

7. Sun Valley, Idaho

Sun Valley combines small-town charm with world-class amenities. Families can enjoy ice skating at the outdoor rink, where you might catch a dazzling ice show featuring Olympic skaters. Take a horse-drawn sleigh ride to Trail Creek Cabin for a cozy dinner, or try your hand at Nordic skiing on over 200 kilometers of groomed trails.

The Sun Valley Museum of History offers insights into the area’s rich past. For a thrilling adventure, go snowmobiling in the Sawtooth National Recreation Area or take a winter wildlife viewing tour to spot elk, moose, and other animals in their natural habitat.

8. Jackson, Wyoming

Jackson offers a perfect blend of Wild West charm and winter wonderland magic. Families can ride horse-drawn sleigh through the National Elk Refuge to see thousands of elk up close. Explore the charming Town Square with its iconic antler arches, or visit the National Museum of Wildlife Art.

For outdoor fun, try snow tubing at Snow King Mountain or take a scenic ride on the Big Red aerial tram for stunning views of the Teton Range. Don’t miss the opportunity to soak in the natural Granite Hot Springs, accessible in winter by snowmobile or dog sled tours.

9. North Conway, New Hampshire

Nestled in the heart of the White Mountains, North Conway offers New England charm and diverse winter activities. Families can enjoy scenic train rides on the Conway Scenic Railroad, offering winter wonderland views from heated carriages. Visit Story Land’s three-acre ice castle, a magical frozen fortress with tunnels, slides, and light shows.

For outdoor adventures, try snow tubing at Cranmore Mountain Resort or explore the winter trails at the Mount Washington Valley Ski Touring and Snowshoe Center. The Mount Washington Observatory Weather Discovery Center provides interactive exhibits about extreme mountain weather.

10. Whitefish, Montana

Whitefish near Glacier National Park offers a quintessential Montana winter experience. Families can explore the charming downtown, filled with unique shops and restaurants. Take a guided snowshoe tour in Glacier National Park to see frozen waterfalls and snow-capped peaks.

Try dog sledding through the Flathead National Forest, or take a horse-drawn sleigh ride at the Bar W Guest Ranch for a unique adventure. The Whitefish Museum provides insights into the area’s railroad and skiing history. Don’t miss the chance to spot wildlife on a winter safari in Glacier National Park, where you might see bighorn sheep, elk, or even wolves against a stunning snowy backdrop.

As these destinations prove, you don’t need to be a skier to experience the enchantment of America’s winter wonderlands. From cozy sleigh rides through snow-covered forests to exploring ice castles and soaking in natural hot springs, these towns offer countless ways for families to create magical winter memories together.

So pack your winter boots (but feel free to leave those skis at home), and get ready to discover the incredible experiences waiting for your family in these snowy mountain towns.

More Winter Travel Tips & Inspiration

Looking for more winter getaway ideas?

Try these magical US winter wonderland destinations
Visit the best of snowy Canada in the winter months
Our favorite winter road trip destinations in New England
Making the Most of the Winter Months in The Midwest
Sensational California road trips you can still enjoy in winter
Enjoy these National Parks with fewer crowds and fabulous views in the winter
Escape for some sunshine and see why Florida is so popular with families for a winter vacation

New England in winter is a magical wonderland, offering a perfect blend of snowy landscapes, cozy towns, and festive cheer. From the twinkling lights of quaint villages to the exhilarating slopes of ski resorts, this region transforms into a winter playground for families.

Whether you’re seeking outdoor adventures, historical explorations, or simply a peaceful retreat, New England’s winter charm is undeniable. Bundle up and hit the road to discover these enchanting destinations that showcase the best of the region from the festive season through early March.

12 Quaint New England Towns to Visit in Winter

2. North Conway, New Hampshire

North Conway serves as a gateway to winter adventures in the White Mountains. This vibrant town is surrounded by natural beauty and offers a perfect mix of outdoor activities and indoor comforts.

Families can enjoy skiing and tubing at Cranmore Mountain Resort or take a scenic ride on the Conway Scenic Railroad’s “Notch Train” for breathtaking views of snow-covered mountains. The town itself is a shopper’s paradise with its famous outlet stores and local boutiques.

Winter is an excellent time to visit as the crowds are smaller, and the snow-covered landscape is truly magical. Don’t forget to visit the Mount Washington Observatory Weather Discovery Center for an interactive learning experience about mountain weather and climate.

3. Mystic, Connecticut

For a coastal winter experience, Mystic offers a unique blend of maritime history and small-town charm. While typically busier in summer, winter brings a peaceful ambiance to this seaside village.

The renowned Mystic Seaport Museum, America’s leading maritime museum, is less crowded and offers special winter programs. Families can explore historic ships, watch ice carving demonstrations, and enjoy seasonal exhibits.

The Mystic Aquarium is another year-round attraction, where you can watch penguins frolic in their outdoor habitat – a fitting winter activity! Downtown Mystic, with its drawbridge and quaint shops, looks particularly enchanting adorned with holiday decorations. Winter in Mystic provides a calmer, more intimate experience of this charming coastal town.

4. Berkshires, Massachusetts

The Berkshires region in western Massachusetts is a cultural haven that takes on a special charm in winter, with several particularly enchanting towns to explore. Stockbridge, which inspired many of Norman Rockwell’s paintings, looks like it stepped right out of a Christmas card with its Main Street’s historic buildings draped in snow.

Nearby Lenox, with its gilded-age mansions and boutique shops, offers old-world elegance, while the creative energy of Great Barrington draws visitors to its vibrant downtown filled with cafes and independent stores.

For outdoor adventure, families can enjoy skiing and snowboarding at Jiminy Peak in charming Hancock, or try cross-country skiing and snowshoeing in Kennedy Park in downtown Lenox.

The region’s cultural attractions shine in winter – visit the Norman Rockwell Museum in Stockbridge or MASS MoCA in the industrial-turned-artistic city of North Adams. Lee, known as the “Gateway to the Berkshires,” captivates visitors with its classic New England architecture and cozy restaurants serving farm-to-table cuisine.

Winter is also a great time to catch performances at Tanglewood in Lenox, the summer home of the Boston Symphony Orchestra, which offers a special winter series. The Berkshires’ combination of quaint towns, natural beauty, and cultural richness makes it a unique winter destination.

5. Portland, Maine

Portland, Maine’s largest city, offers a vibrant urban experience with a side of coastal winter beauty. The historic Old Port district is particularly charming in winter, with its cobblestone streets and 19th-century brick buildings dusted with snow. Families can enjoy ice skating at Thompson’s Point, followed by hot cocoa at a local café. The Portland Museum of Art provides a warm retreat on cold days, offering an impressive collection of American, European, and contemporary art.

Winter is an excellent time for foodies to visit, as Portland’s renowned restaurants are less crowded, allowing for a more relaxed dining experience. Don’t miss the chance to take a winter wildlife watching cruise in Casco Bay to spot seals and winter seabirds. Portland’s mix of urban amenities and natural beauty makes it a unique winter destination.

6. Newport, Rhode Island

Newport, known for its Gilded Age mansions, takes on a different character in winter. The opulent Newport Mansions are decorated lavishly for Christmas through early January, offering a glimpse into how the wealthy celebrated the holidays in the past. The annual Newport Winter Festival in mid-February is a highlight, featuring ten days of music, food, and family activities.

Ice skating at the Newport Skating Center, with its harbor views, is a must-do winter activity. For a unique experience, take a seal watch cruise to spot these playful creatures in their natural habitat. Winter in Newport means fewer crowds and lower prices, allowing families to enjoy this luxurious destination more affordable.

7. Woodstock, Vermont

Woodstock epitomizes the charm of a New England winter. This picturesque town is especially magical during the holidays, with its annual Wassail Weekend in December featuring horse-drawn wagon rides, a holiday craft fair, and caroling.

For winter sports enthusiasts, the nearby Saskadena Six Ski Area offers family-friendly skiing and snowboarding. Cross-country skiing and snowshoeing trails abound in the surrounding countryside.

Don’t miss the chance to visit the Billings Farm & Museum, a working dairy farm that offers special winter programs and sleigh rides. Woodstock’s covered bridges and colonial architecture look particularly stunning under a blanket of snow, making it a perfect setting for a winter family getaway.

8. Lake Placid, New York

While technically not in New England, Lake Placid in the Adirondacks is worth including for its exceptional winter offerings. As a two-time host of the Winter Olympics, it’s a paradise for winter sports enthusiasts. Whiteface Mountain offers world-class skiing and snowboarding, while the Olympic Sports Complex provides opportunities to try bobsledding and ski jumping.

In February, the Empire State Winter Games bring exciting competitions and festivities. Families can also enjoy dog sledding, ice skating on Mirror Lake, or a peaceful cross-country ski through the surrounding forests. The charming Main Street, lined with shops and restaurants, offers a cozy retreat after a day of outdoor adventures.

9. Bretton Woods, New Hampshire

Bretton Woods is New Hampshire’s largest ski area and a premier destination for winter sports. With 464 acres of skiing and snowboarding terrain, it’s suitable for all levels. The resort also offers a range of other winter activities, including sleigh rides, fat biking, and one of the largest Nordic centers in the east for cross-country skiing.

Families can enjoy the Bretton Woods Canopy Tour, a thrilling zip-line experience that operates year-round. The historic Mount Washington Hotel, with its grand architecture and stunning mountain views, is especially cozy in winter. In January and February, look out for special events like torchlight parades and fireworks displays.

10. Tuckerman’s Ravine/Jackson, New Hampshire

Jackson and the surrounding Mount Washington Valley area offer some of New England’s best sledding and snow-tubing adventures. The centerpiece is Jackson XC, one of the most renowned cross-country ski centers in the East, but it’s the variety of non-ski winter activities that make this area special.

Families flock to the historic Jackson Village Hill, a natural slope that’s been delighting generations with its perfect sledding conditions since the 1920s. The nearby Great Glen Trails Outdoor Center offers snow tubing, winter fat biking, and snowshoeing adventures with stunning views of Mount Washington.

For a unique experience, take a ride on the Mt. Washington SnowCoach, a specially-equipped van that climbs the snow-covered Auto Road. In February, don’t miss the annual Return of the Old Man Winter Festival, featuring ice sculpture contests, sledding races, and family-friendly activities.

12. Kennebunkport, Maine

Kennebunkport, a popular summer destination, becomes a magical winter retreat during the colder months. The annual Christmas Prelude in early December transforms the town into a holiday wonderland with tree lighting ceremonies, carol singing, and Santa arriving by lobster boat. Even after the holidays, the town retains its charm with cozy inns, art galleries, and restaurants perfect for warming up on cold days.

Winter beach walks along the dramatic coastline offer a peaceful escape, while nearby Harris Farm provides opportunities for cross-country skiing and snowshoeing. In February, the town hosts its Paint the Town Red event, celebrating Valentine’s Day with special dinners, wine tastings, and other romantic offerings that families can also enjoy.

There’s nothing quite like fall in New England. As the summer sun begins to fade, we begin to crave the feeling of crisp fall air, the tastes of freshly harvested apples, cranberries and pumpkins, and, of course, the beautiful fall foliage.

One of our favorite ways to experience this magical time of year is by taking a New England road trip. 

Typically, fall in New England runs from September 1st through late October. It’s during this time that you’ll find a number of family-friendly festivals celebrating the sights, sounds, and tastes of the season. It’s also when leaves change colors and create brilliant landscapes of yellow, orange, and red. 

Peak fall foliage generally takes place between the last weekend of September and Columbus Day. For specific information on locations and the changing of the colors check out foliage trackers like ExploreFall.com.

5 Day New England Fall Road Trip  

With Logan International Airport Boston being a big international hub airport, we have designed our New England road trip itinerary with this starting point. Next, you’ll head west to the Berkshires, up north through Vermont, and then east to the Acadia on the coast, by way of the White Mountains of New Hampshire. 

You can complete the drive from Bar Harbor back to Boston following this itinerary.

Since this trip is all about seeing the beauty of fall in New England, remember that leaves change earlier in the season, the further north and inland you are. So, if you’re visiting later in the fall, the suggestion would be to start in the north and work your way south. 

Day 1: Boston & Cape Cod, Massachusetts

There’s no better way to start an epic New England Road Trip than with a day in the great city of Boston. 

Fall is the perfect time of year to explore all the historic sites of this great city. Walk the Freedom Trail, stroll through Boston Commons, and check out the big ships in the harbor. If the weather is a little bit iffy, kids will love to visit the New England Aquarium and see all the underwater creatures. 

Boston is also a great home base to explore the surrounding area. Salem, Massachusetts, is a mere 30 minutes from downtown and has so much fun during the Halloween season. 

Driving south from the city, it’s easy to spend a day exploring Cape Cod as the fall colors change in the season. The whole family will love exploring the towns on the cape and walking along the sandy beaches. Don’t miss a visit to the Whydah Pirate Museum in West Yarmouth.

Fall on the Cape is tons of fun, with the Harwich Cranberry & Arts Festival in September and the Yarmouth Seaside Festival in October. Both are tons of fun for the family, with music, vendors, and fireworks. 

Stay overnight in Cape Cod – search suggestions here!

Day 2: Berkshires, Massachusetts

In less than a three-hour drive west on I-90 it’s on to the second leg of this New England road trip, The Berkshires. Set in Western Massachusetts, this landscape is an escape into nature any time of year. But fall foliage transforms the area to be even more breathtaking.

Any New England road trip should plan for at least a day in the Berkshires. Here, it’s easy to fill your fall road trip itinerary with outdoor activities like hiking, biking, and even horseback riding.

In the fall, the whole family will love picking apples or pumpkins and sipping cider at places like Bartlett’s or Furnace Brook Winery at Hilltop Orchards. The Naumkeag Pumpkin Show in Stockbridge is a favorite with families throughout October.

The Berkshires are known for their excellent Farm-to-Table culture. They have wonderful restaurants and farmers’ markets. Towns like Pittsfield, Lenox, and Williamstown have excellent markets to explore through October. 

For outdoor adventures like ziplining and alpine sliding, head to Jiminy Peak or Berkshire Eastern Mountain Resort.

Staying overnight we recommend Stockbridge – search suggestions here!

Pro Tip: The Berkshires are also the perfect place to camp. With dozens of campsites in the area, it’s easy to find the one for you, including RV hookups like at Fernwood Forest Campground. 

If you have a little longer in the state, Massachusetts also has a number of incredible scenic drives, including the Mohawk Trail in the Berkshires youcould add to this itinerary, time permitting. 

Day 3: Burlington, Vermont

Nothing quite compares to Vermont in the fall. The Green Mountains are picturesque as they change colors from green to brown, orange, and yellow. There’s no better way to enjoy the season than taking a New England fall road trip to Burlington with your family. 

The drive from the Berkshires to Burlington takes only about three and a half hours without stopping. But instead of rushing along, we recommend stopping off at Woodstock (VT, not NY) and Montpelier. Both are quintessential Vermont towns and are postcard-perfect in the fall.

An excellent family activity is visiting the Ben & Jerry’s ice cream factory, just a short distance from Burlington. No matter your age, you’ll love learning about Ben and Jerry’s journey to becoming the kings of ice cream.

In Burlington, don’t miss exploring Church Street Marketplace, walking along the shore of Lake Champlain on the Greenway, or enjoying any of the great restaurants in town. 

The Lake Champlain Byway is one of the most scenic drives in Vermont and runs through Burlington. Check out this and other scenic drives in the state. 

Pro Tip: On the drive between Berkshires and Burlington, take a detour to check out the Vermont Wine and Harvest Festival in West Dover. 

Best places to stay in Burlington – search suggestions here!

Stowe, Vermont, is another favorite place among leaf-peepers, and it’s less than an hour from Burlington, making for a convenient detour on your New England fall road trip. With extra time in your itinerary, we’d suggest staying an additional day in the area and heading up the Gondola SkyRide at Stowe Mountain Resort.

Day 5: Acadia National Park & Bar Harbor, Maine

On the final leg of this splendid New England fall road trip, set your sights on Acadia National Park and Bar Harbor, Maine. 

Coming from New Hampshire, the drive should take just under four hours. If you’re not in a huge rush, consider going by way of Rangeley Lakes National Scenic Byway. It’s one of the best parts of driving in New England.

Once you arrive, you’ll understand why Acadia National Park is one of the most visited parks in the country. Visiting this beautiful landscape is a bucket list item and a must on any fall road trip itinerary. Besides the gorgeous fall colors, visiting Acadia in the fall means fewer crowds but colder temperatures.  

Many come to Acadia to hike the picturesque terrain but there are plenty of scenic driving routes to enjoy, too. The Acadia Byway (Route 3) will take you onto Mt. Desert Island around the park and to Bar Harbor. 

Driving up Cadillac Mountain is a favorite New England fall road trip activity that is permitted until late October. Vehicle reservations are required to drive to Cadillac Summit, so ensure you’ve reserved this journey in advance (30% of reservations go on sale 90 days in advance, the remaining reservations open 2 days in advance).

If the timing aligns, the Acadia Night Sky Festival and Acadia Oktoberfest are two great things to add to your New England fall road trip itinerary. 

The historic coastal town of Bar Harbor is the perfect place to stay when visiting Acadia. There are plenty of places to stay, small shops and quaint restaurants. As the season winds down, so does the town. So, it’s best to visit in September and October. 

Pro Tip: Acadia National Park requires an Entrance Pass. Get yours in advance on the NPS website, or if you have a 4th grader in the family, you could be eligible for free entry!

Best places to stay in Bar Habor – search suggestions here!

If you love the scenery in Maine, why not go further on these 7 incredible scenic drives in the state?  

Consider driving along the Atlantic Coast to Boston when heading south from Acadia National Park. You’ll love the quaint seaside towns and the view from the road. Make sure to stop off at the historic town of Portsmouth. It’s one of the best places to visit New Hampshire in the fall, plus a stop at Take Flight Aerial Adventure Park is bound to be a must for the kids.

With an extra day or 2 available, don’t rush the journey back. Instead, follow our coastal itinerary from Boston to Bar Harbor in reverse. 

More Tips For A 5 Day New England Fall Road Tripping 

Knowing the fall foliage schedule is essential for the perfect New England road trip. The following sites have some of the best info:
Individual states post their own yearly foliage maps like New Hampshire, Maine and Vermont
The Farmers Almanac uses historical data to predict the foliage schedule 
Peak fall foliage happens earlier in the north and inland. So, it’s ideal to visit places like Burlington, Vermont in September.
Visiting New England during the fall is super popular so make sure to arrange accommodation well in advance, particularly on weekends. 
Always stay up to date on weather and road conditions as things can rapidly change; New England 511 is an excellent resource to keep saved on your phone as it covers road conditions for the entire region. 
Find more inspiration here for fall getaways on the East Coast – plus don’t forget you can head a little further north and enjoy the best of fall in southern Canada, too.

When the temperature starts to drop, the leaves begin to change, and the scent of pumpkin spice begins to take over, we all know that autumn has started. There’s no better place to be than New England in the fall. From Maine to Connecticut, the entire region comes alive to celebrate the fall season.

The best way to experience it all is to pack the car and set off for an epic New England fall road trip. But where to go?

Here, we’ve mapped out 4 epic fall road trips in New England. You’ll find itineraries that take you along the coast and others deep into Mother Nature. No matter which you choose, you’ll be in for a beautiful autumn in New England. 

Before we dive into our road trip itinerary suggestions, you may also want to read:

Our top tips for driving in fall road conditions. This includes weather patterns to be aware, car maintenance to keep in check and what to pack in your car for a fall foliage drive
Stylish yet comfy outfits to pack for your fall drive in New England

New England Fall Road Trip Maps

1. Berkshires to Burlington (US-7N)

• Distance: 219 miles  
• Time needed: 5 hours to 3 days

If you want to experience the majesty of the mountains as they change colors with the cooler temps, there’s no better New England fall road trip than the Berkshires to Burlington. 

Beginning in the West Massachusetts town of Sheffield, hop on route US-7 North for one of the most scenic drives in New England. You’ll travel through the beautiful region of the Berkshires, where outdoor adventure awaits, like hiking, biking, and even camping. Local farms along the way provided family fall fun with pumpkin patches and apple cider. 

Heading north into Vermont, Route 7 meanders through quaint New England towns like Bennington and Middlebury. Throughout the trip, you’ll love exploring historic towns, taking in the beautiful landscape, and seeing the covered bridges in the region. Bennington alone has 5, including Paper Mill Village and Silk Road Covered Bridges.

At the northern end of Route 7 is Burlington, Vermont. As the largest city in the state, there’s tons to do, especially on a fall road trip. Situated along the shore of Lake Champlain, walking or biking the Greenway is a definite must.

Church Street is where you’ll find everything from great restaurants and shops to live music and nightlife. There are even fun events throughout the fall, like the Howl’ween Dog Costume Contest and Family Art Saturday. 

The best of fall foliage on this road trip in New England typically begins in Northern Vermont in mid-September. To the south, early October is peak foliage time for the Berkshires. 

If you’re looking for even more fall fun, extending this New England road trip to Stowe is easy and rewarding. It’s only 40 mins from Burlington and is one of the best scenic drives in Vermont. Simply take I-89S to VT-100 N in the historic village of Waterbury.

You’ll pass right by Ben & Jerry’s ice cream factory, where you can take a tour and sample the delicious dessert. At Stowe Mountain Resort, you can climb Mt. Mansfield by hiking, on the Gondola SkyRide, or driving the Auto Toll Road. 

2. Coast of Long Island Sound to Cape Cod (I-95 N, US-1N, I-195E, US-6E) 

• Distance: 269 miles  
• Time needed: 5 hours to 3 days  

One of the absolute best scenic drives in New England is along the shore of Long Island Sound through Connecticut, Rhode Island, and up to Cape Cod. It’s a fabulous trip just about any time of year, but there’s something special about doing it in autumn. It’s when you’ll experience both the magical fall foliage and the tranquil sailboats on the water. 

Beginning in Greenwich, Connecticut, you’ll travel I-95 N along the coast. Make sure to get off and visit the many quaint coastal towns. The fall foliage in this area normally peaks in mid-October through November.

Definite must-dos along the Connecticut coastline are visiting the Mystic Seaport Museum (a family favorite), strolling along the Saugatuck River in Westport, and exploring Main Street in Old Saybrook. This section of the trip is one of the best scenic drives in Connecticut. 

After crossing the border into Rhode Island, set the course for Newport. This historic seaside town is tons of fun for the entire family. There’s lots to explore right on the water’s edge in Newport, making it one of the best scenic drives in Rhode Island.

Watch the boats in the harbor before learning all about it at the Sailing Museum. Get into the fall season in Newport by picking pumpkins and getting lost in a corn maze at local farms. You can even take a Ghost Tour in town. Newport is a great place to spend the night. You’ll find a range of accommodations that meet just about every budget and need. 

The final destination on this coastal New England fall road trip is Cape Cod. The whole family will love exploring the sandy beaches and historic towns. The Cape comes alive in the fall, with the peak fall foliage happening between late September and mid-October. It’s also when events like the Yarmouth Seaside Festival take place. 

Pro Tip: Although you’ll miss the massive summer crowds, Cape Cod is still a super popular destination in the fall. So try to avoid the peak traffic times of Friday evening and Sunday afternoon.

3. Bar Harbor to Boston (I-95S)

• Distance: 281 miles  
• Time needed:  4.5 hours to 3 days  

One of New England’s best places to experience fall is the great Acadia National Park in Maine. Driving the park’s Loop Road through Desert Mountain Island and Bar Harbor is one of the best scenic drives in Maine. So, starting a fall foliage road trip from here makes sense. 

After the summer crowds calm, a new crop of visitors make their way to Acadia in the early fall. The best time to see fall foliage is mid-September until mid-October.

One of the best ways to see the beautiful landscape is from the top of Cadillac Mountain. When considering where to stay, there’s everything from camping in the park to more traditional accommodations in Bar Harbor. Remember that in mid-October, most of these options close for the season.

Pro-Tip: Purchase your entrance pass to Acadia National Park ahead of time at Recreation.gov.

After Bar Harbor and Acadia, it’s time to explore more of beautiful New England in the fall. Head south on I-95 towards Portsmouth, New Hampshire, a definite stop on one of New England’s best fall road trips.

This seaside town has tons to discover, including historic sites and unique boutiques in Market Square. Everyone in the family will love exploring the past at Strawbery Banke Museum.

Leaving Portsmouth, follow the New Hampshire Coastal Byway (NH Routes 1A and 1B) south rather than taking I-95. It’s one of the most scenic drives in New Hampshire, taking you to Seabrook along the shore and through both North Hampton and Hampton Beach State Parks. 

Pro Tip: New Hampshire State Parks have free entry but require metered parking.

The final leg of the drive is along the northern coast of Massachusetts on the Essex Coastal Scenic Byway, one of the best scenic drives in the state. This beautiful trip includes a ton to explore and appreciate, including small seaside towns like Salisbury and Newbury.

Along the Shore of Cape Ann, the whole family will appreciate making stops in Gloucester to spot whales off the shore and Essex to visit the Shipbuilding Museum. 

No fall trip to New England would be complete without a visit to Salem, Massachusetts. Lucky for us, it’s a stop on this epic road trip. Celebrating Halloween for the entire month of October, the town hosts Haunted Happenings with fun family events like Witch Trial reenactments, ghost tours, and magic shows. 

We share more spookily good Halloween-focused New England drives over here!

There’s no better way to complete one of New England’s best fall road trips than in Boston. This historic city is fun all year long, but it is especially beautiful when covered in fall colors.

You’ll love enjoying the city, like strolling Boston Common and Quincy Market in the crisp fall air. Peak fall foliage normally happens around the 3rd week of October, so make sure to plan your New England road trip in time to see it. 

You can easily complete this itinerary in reverse from Boston to Bar Harbor – we share all our favorite coastal stops if you’d like to focus more on Maine

4. Kancamagus Highway, New Hampshire (Route 112)

• Distance: 58.3 miles  
• Time needed: 1.5 hours to 2 days

The Kancamagus Highway (aka “The Kanc”) is one of the absolute best scenic drives in New Hampshire. Even more so, it’s one of New England’s most incredible fall road trips. 

Stretching from Bath across the White Mountains to Conway in the east, The Kancamagus Highway is one of New England’s best places to experience autumn.

A great place to stop on this fall road trip in New England is Loon Mountain. You’ll find outdoor fun like ziplining and festivities like the Highland Games and Oktoberfest. 

A definite must-visit along the Kancamagus Highway is the Franconia Notch State Park. This awesome park has so much to do for the entire family. Here, you can hike the Appalachian Trail, ride the aerial tramway at Cannon Mountain, and even visit the New England Ski Museum. The Flume Gorge is a must on any trip to the park. 

When it comes to where to stay along The Kanc, camping is a great option with 6 different campgrounds plus options at Franconia Notch State Park. Most campsites are open until mid-October. If that’s not really your thing, you’ll find more accommodations near Bath, Lincoln, and Conway. 

Pro Tip: The beauty of the Kancamagus Highway is its immersion into nature. However, that also means that amenities like gas stations and cell service are few and far between. So, make sure to download maps and fill up before you head out on this scenic New England road trip. 

More Fall Road Tripping Tips and Inspiration

Keep reading if you’re looking for even more inspiration for falling road tripping!

Peak fall foliage in New England typically happens around Columbus Day, which is a very popular time, so be sure to have you accommodation booked in advance.
Look out for individual state yearly foliage maps like New Hampshire, Maine and Vermont – or we’ve found the interactive map on explorefall.com to be extremely good
Want the planning work done for you? We have set up this 5 day New England Fall Road Trip Itinerary to help you get the most out of a continuous road trip around the US Northeast
Beyond just New England, these destinations on the East Coast make fabulous fall trips with the family
Or heading further west, these are some sensational spots in the Midwest to experience the magic of fall colors
Take your journey even further, nature lovers you’ll want to seek out these incredible US National parks perfect in Fall, not just famous for their colors but fewer crowds and cooler conditions
Late to the game? Not to worry if you think you’ve missed the peak season in New England, leaf-peppers can still find an incredible array of colors in these late fall drives in the USA