Boston to Bar Harbor, Maine: Explore the Beauty of A Maine Coastal Road Trip

Have you always dreamed of visiting coastal Maine with your family, and now you want to make it a reality? 

We’re right there with you! Maine is one of the most beautiful places in America, and coastal Maine has long been one of the most popular summer vacation spots. It’s filled with towering cliffs, majestic mountains, miles of pristine beaches, and plenty of opportunities to enjoy a good lobster roll. 

The best part is that you can drive from Boston to Bar Harbor in less than five hours (although we recommend taking your time!). 

We’ve created the perfect Boston to Maine itinerary to help you plan the perfect road trip along Maine’s coast, complete with the best attractions for everyone in your family. So what are you waiting for? Let’s hit the road! 

What is the Distance From Boston to Bar Harbor

The shortest distance from Boston to Bar Harbor is 285 miles. The trip takes roughly four hours and thirty-five minutes direct, with the bulk of the drive being along I-95.  

Coastal Maine is filled with quaint fishing villages and photo opportunities, and our itinerary has you stopping at some of the most beautiful places along the way. 

While you can make a direct drive in a day, we encourage you to make plenty of stops along the way. You won’t regret it! 

How Long Do I Need Driving From Boston to Bar Harbor? 

Your drive from Boston to Bar Harbor can be as brief or as long as you’d like for it to be. While we suggest that a bulk of your days be spent in Bar Harbor, you can also take a day at each stop to savor all of the unique opportunities each town has to offer. 

We recommend taking at least 3-5 days to drive to Bar Harbor and then another 2-3 days at your final destination in order to take full advantage of this road trip to Maine. 

Map of stops between Boston and Bar Harbor with collage of images from this coastal drive

Best Time of Year to Drive From Boston to Bar Harbor

The best time to visit coastal Maine is late spring to early summer. However, if you want to avoid large crowds at popular tourist destinations, plan your drive to Maine between May and mid-June or after Labor Day. Otherwise, aim for any time between May and September. 

While locations like Acadia National Park are open year-round, many tourist attractions are only open seasonally, including quite a few of the most popular restaurants and excursions. So if you plan on driving from Boston to Bar Harbor in the fall or winter months, we suggest calling ahead to see what’s available. 

Best Stops on a Boston to Bar Harbor Road Trip

Time to hit the road, here are the top stops from Boston to Bar Harbor we’d make time for in your itinerary:

Kittery

Your first stop in Maine is the charming town of Kittery, just over the bridge from Portsmouth, New Hampshire. Founded in 1623, Kittery has no shortage of historical places to visit and natural beauty to explore. We recommend taking at least a day to take in what Kittery has to offer before continuing on with your trip up the Maine coast. 

USA Maine Road Trip - Kittery

Take a ferry boat tour of Portsmouth Harbor and the Piscataqua River, where you can take in the sights of Pepperrell Cove, Kittery Point, and Whaleback Light. Or travel on the Memorial Bridge to explore Badger’s Island before visiting Seapoint Beach and Fort McClary. 

If you’re travelling with children, spending an hour or two at the Take Flight Aerial Adventure Park is sure to burn some of that pent-up travel energy! Choose from over 65 activities to climb and even go on a zipline tour! 

Lastly, don’t forget to enjoy some much-deserved retail therapy at Kittery Premium Outlets, featuring several of the best outlet stores in New England. Then grab a bite to eat at one of Kittery’s many fine restaurants, including Robert’s Maine Grill, Chauncey Creek Lobster Pound (a local favorite), or Captain and Patty’s. If you plan on staying the night, the historic York Harbor Inn in nearby York is an excellent option. 

York

Just a 10-minute drive from Kittery, the town of York is actually made up of four different communities; York Village, York Harbor, York Beach, and Cape Neddick. You can easily take in the sights of “The Yorks” in a day before continuing on your Maine road trip without feeling like you missed out on anything. 

USA Maine Road Trip - York

Visiting York Beach is an absolute necessity, if for no other reason than getting a sweet treat at The Goldenrod, a historic candy shop, and cafe that’s been around since 1896. Load up on snacks to take with you to Long Sands Beach, a popular swimming and sunbathing spot. 

If you’re traveling with children, Short Sands beach may just be the place to go. This quarter-mile stretch of sand is surrounded by cliffs, is near a playground in Ellis Park, and also houses Fun-O-Rama, an arcade right there on the sand! 

Pick up some delicious specialty foods and souvenirs from Stonewall Kitchen York Company Store before taking the family to York’s Wild Kingdom, New England’s only zoo AND amusement park. Your kids will love seeing kangaroos, zebras, and even African lions. You can easily spend a few hours of fun, and it’s a perfect stop to add to your Boston to Maine itinerary. 

Ogunquit

No Maine coastal road trip would be complete without a stop in Ogunquit, another 10 minutes away from York. You can easily take at least a day to explore all that Ogunquit has to offer, including beaches, museums, performing arts, and more. 

USA Maine Road Trip - Ogunquit

Spend a few hours of pampering at the Cliff House Resort before taking a walk down Marginal Way, a 2.5-mile paved path that provides plenty of photo opportunities and views of the sea. Marginal Way takes you right to Perkins Cove, a picturesque fishing village on the Maine coast full of shops, restaurants, and artisans. 

Go on a whale-watching excursion with Finest Kind or simply relax at Ogunquit Beach. It was voted one of the top 25 beaches to visit in the U.S., and for a good reason. The pristine sand and foaming waves are perfect for strolling, kayaking, or just splashing in the cool water.  

There are also several can’t-miss seasonal activities in Ogunquit, like The Ogunquit Playhouse, a summer theater program. Or you can explore the Ogunquit Museum of American Art, a gorgeous location overlooking the ocean and filled with a richly varied depiction of Maine’s history. 

Kennebunkport

You must schedule in at least a day of your Maine coastal road trip to enjoy the wonders of Kennebunkport, the summer retreat of the Bush family, and a true Maine treasure. Book a stay in the historic Dock Square area at one of the Captain’s Collection. These stately ship captains’ homes have been converted into luxurious resort-style accommodations for every family. 

USA Maine Road Trip - Kennebunkport

Next, explore Dock Square, the hub of Kennebunkport. This area is full of local boutiques and artisan shops, famous restaurants like Striper’s (a Bush family favorite), the Clam Shack, and Old Vines Wine Bar. It’s the perfect place to find one-of-a-kind treasures and souvenirs. 

History buffs will enjoy the impressive sea captains’ mansions along Summer Street and local museums like the one featuring the First Family exhibit at White Columns at 8 Maine Street. The Brick Store Museum and Nott House are also worth exploring, and children will love the Seashore Trolley Museum. 

Whale watching is a popular Kennebunkport tourist attraction, one of many boat tours available along the coast. You can also rent kayaks, canoes, and bikes from several locations in town and choose your own adventure. Snap a pic of Goat Island Lighthouse from Cape Porpoise, fish for stripers on Colony Beach, or take in the breathtaking scenery at Goose Rocks Beach before continuing on your way.

Old Orchard Beach

Drive another half hour and you’ll reach Old Orchard Beach, an essential stop on your Boston to Maine itinerary. Also known as OOB, this scenic spot has been voted Maine’s Best Beach year-over-year, and it’s easy to see why. Your kids will love splashing in the gentle waves, building sandcastles, and enjoying an oceanfront amusement park complete with an old-fashioned carousel. 

USA Maine Road Trip - Old Orchard Beach

The Pier is a popular tourist spot and offers plenty of places to eat delicious food and enjoy cool drinks. Walk 500 feet out into the Atlantic and take in the gorgeous ocean views, live entertainment, and fireworks every Thursday night during the summer. 

There are also several opportunities to explore Old Orchard Beach on the water, whether you’re interested in lobstering tours, fishing excursions, or rafting tours. You can also navigate the Saco River and Scarborough salt marsh by canoe or kayak (if you’re feeling bold!). 

If you have children, visiting Palace Playland is an absolute must. It’s the only oceanfront amusement park in New England, and it’s full of classic rides like a Ferris wheel, roller coasters, and plenty of fun games and tasty fair food. We recommend spending a few hours there before nap time and letting the kiddos sleep on the drive to Cape Elizabeth! 

Portland

Not only is Portland the largest city in Maine, but it’s also one of the best Maine coastal towns to visit. There’s something for everyone here, so you’ll want to spend a few days taking advantage of everything that Portland has to offer. From oceanside strolls to five-star restaurants, this unique coastal city has it all. 

USA Maine Road Trip - Portland

You’ll want to spend at least a half-day in Old Port district browsing boutiques and crafts from local artisans. The cobblestone streets and stately architecture are straight out of the early 20th century, but there is also a very modern feel to the architecture. Experience one of the last remaining working waterfronts in the United States by walking along Commercial Street and tasting freshly caught lobster and fish at several of Portland’s seaside restaurants. 

There are so many fun and exciting things to do in Portland and nearby Cape Elizabeth, like taking a lighthouse tour ferryboat ride or visiting the nearby islands by way of the Casco Bay Ferry Lines. Then, explore Fort Williams Park and see the Portland Headlight, an iconic Maine lighthouse. Just make sure you get a dish of ice-cold gelato at Gorgeous Gelato before moving on. 

Freeport

Next up on your trip from Boston to Maine is Freeport, a classic Maine tourist destination. You can easily spend at least a day in Freeport, as there are many opportunities to shop, enjoy mouthwatering seafood, and explore this historic coastal town. 

USA Maine Road Trip - Freeport

Learn the fascinating history of Freeport by taking a Red Cloak Tour, where you can choose from a selection of different tour options to fit your interests. The Maine Maritime Museum on the Kennebec River is also a treat for family members of all ages, with a range of interesting exhibits, lighthouse cruises, a fishing schooner, and even a kids’ pirate play ship! 

Stop for a sweet treat at Ben & Jerry’s ice cream before doing a little window shopping at Freeport’s many boutiques, antique stores, art galleries, and our favorite, L.L. Bean’s massive flagship store! Then, break in those new hiking boots by walking Brimstone Hill Trail before sitting down to eat at one of Freeport’s many fabulous restaurants. We recommend Harraseeket Lunch & Lobster Co., a family-owned Freeport favorite with the freshest lobster rolls in Maine! 

Boothbay Harbor

Boothbay Harbor is a welcome stop on your way from Portland to Bar Harbor, and it’s a beautiful place to stop and relax along the Maine coast. This storybook town is a walker’s paradise, with so many shops, trails, and of course, the Boothbay Footbridge, you’ll need at least a day to take in all the sights! 

USA Maine Road Trip - Boothbay Harbor

Boothbay Harbor is famous for its boat excursions and has earned the title of Boating Capital of New England. Take a harbor tour to see nearby Burnt Island and Monhegan Island, and you can even get up close and personal with whales, seals, and puffins! Boothbay Harbor also offers some of the best sea kayaking in Maine, and you can rent kayaks at several shops along the shore. 

There are many kid-friendly activities in Boothbay Harbor, such as the Boothbay Railway Village. There, your children can go on a narrow-gauge railway ride before heading over to the Maine State Aquarium. Kids can touch live lobster and starfish in the aquarium’s petting tank and learn all about Maine’s fascinating marine life. 

Boothbay Harbor is the perfect spot to stop for the night, and there is no shortage of seaside inns and resorts that offer stunning ocean views and all the comforts of home. You’ll also find a wide range of eateries to satisfy even the pickiest of eaters, and you’ll definitely want to top off dinner with some Maine-made ice cream. Kaler’s Restaurant is the area favorite for fresh, affordable seafood, while the Blue Moon Cafe is one of the best breakfast spots in town. 

Bar Harbor

Last but not least on our Boston to Maine road trip itinerary is Bar Harbor! Otherwise known as the gateway to Acadia National Park, Bar Harbor has been one of America’s most popular summer vacation destinations for over 100 years. As such, there are seemingly endless things to see and do, so we recommend spending at least three to four days at this conclusion of your Maine road trip. 

USA Maine Road Trip - Bar Harbor

Summer is the best time of year to visit Bar Harbor, whether you’re whale watching, hiking the trails, or relaxing on the seashore. Book a room at one of the town’s many historic bed and breakfasts, or rent a cottage on Mount Desert Island. There are countless accommodations to suit any preferences or family size, and they’re all equally beautiful. 

Remember the Red Cloak Tours in Freeport? Bar Harbor also offers five unique Red Cloak walking tours for the whole family. Pirate’s Cove Adventure Golf is also a popular pastime, as are the Bar Harbor Ghost Tours.

You can also enjoy cruises, ferryboat rides, lobster fishing, and seal watching (just to name a few). Bar Harbor truly is a treat, and it’s the perfect way to end your adventure up the Maine coast. 

More Tips for Road Tripping in Maine

  • As beautiful as Maine is, you’re still going to encounter plenty of bugs. Mosquitos, blackflies, and moose flies can quickly become annoying, so pack an effective bug spray like Avon Skin So Soft Bug Repellent
  • Will you be trying lobster for the first time while you’re in Maine? If so, we recommend a seaside restaurant or clam shack along the coast where you can sit outside, roll up your sleeves, and dig right in. 
  • You’ll be doing plenty of walking, hiking, and seaside strolling during your Maine road trip, so pack a pair of durable walking shoes and closed-toe hiking sandals. 
  • Depending on the time of year, you’re likely to encounter a moose or two while out in nature. While majestic, moose are not particularly friendly, and you want to give them a wide berth. 
  • Regardless of how many days you’re taking for your Boston to Maine road trip, we recommend going on a boat tour at one of your stops. Maine’s ocean life is fascinating, and you won’t regret it! 
  • We know how stressful packing can be, and that’s why we created our Ultimate Family Road Trip checklist. It certainly makes packing a much more organized process. 

© Family Road Trip

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