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Planning the Ultimate Road Trip From Boston to Kennebunkport

Two people driving in a car on a road trip at sunset
Our Guide to Road Tripping From Boston to Kennebunkport

Nestled 90 miles north of the bustling streets of Boston is the quaint coastal town of Kennebunkport. Zoom up Interstate 95 for a quick route to relaxation or enjoy a leisurely drive along the coast to take in the sights. Indulge in fresh Maine lobster. Sample the local craft brews in Portsmouth. Visit New England’s iconic lighthouses. Satisfy the burning hole in your pocket with some retail therapy at the Kittery Outlets. 

Everything You Need to Know About Road Tripping From Boston to Kennebunkport

Essex Street Pedestrian Mall

Right outside of the congested Bean Town streets is Essex Street Pedestrian Mall. You’ll find the open air market 20 minutes off of I-95 towards Salem. Start at the Peabody Essex Museum and discover art from the 1700s to the present day. Cruise down the tree-lined streets, meet with local vendors, learn about the rich history of Salem, and grab a bite to eat at one of the mall’s unique restaurants.

Cape Ann Museum and Gloucester Harbor

Cape Ann Mass view of fishing boats

Take a stroll through Gloucester Harbor. The working port is busy, but it’s truly a unique experience. Visit the Gloucester Fisherman’s Memorial or sit on the shore and enjoy whale watching off the choppy coast. Plug in your earbuds and enjoy a walk through history with Gloucester’s self-guided harbor walk.

Portsmouth, NH

The coastal town of Portsmouth is buzzing with activities. Stretch your legs with a stroll along the waterfront, have lunch or dinner at one of the many craft restaurants, or plan accordingly to catch a show on your way up north. Here are a few suggestions on planning your stop in Portsmouth when heading to Kennebunkport.

Great Rhythm Brewing Company

Great Rhythm is the perfect quick stop before dinner. It boasts an airy taproom and several seasonal brews available for on-site tastings. The Hi-Fi and Sticky brews are two local favorites. There’s not an overwhelming list, so choose your favorite and then take a few cans with you to enjoy in the Kennebunks.

The Music Hall

The Music Hall downtown has been entertaining Portsmouth since 1878. The venue hosts theatre shows, concerts, on-screen performances, and comedy programs. With performances nearly nightly, they’re likely to have something going on when you come through. Check their calendar of events for the latest information.

Isles of Shoals

If time allows, plan a day trip to the Isles of Shoals. Isles of Shoals Steamship Company provides daily cruises through the island chain. Listen to the stories about Captain John Smith and Pocahontas. Arr along pirate tales about Blackbeard and Scottish sailor turned pirate, Captain Kidd. White Island is the home to Isles of Shoals’ Lighthouse, so don’t forget your camera for this trip.

Chauncey Creek Lobster Pier

lobster dinner

The concept at Chauncey’s is simple—order the main, bring everything else. They have two menus, fried and lobster. Grab an order of fish bites if you’re hungry enough, but save room for lobster. This is a laid back spot so show up in flip flops, pick one of their brightly painted tables, uncork a bottle of wine, and bask in the Atlantic sun.

The Kittery Outlets

Curb your shopping addiction with a stop at Kittery Outlets. Just an hour outside of Boston, the outlets offer over 120 brand names with unbeatable prices. It’s the perfect place to find some new beach gear. Grab a bite to eat or a cup of coffee at one of their five on-site restaurants before hopping back on the road.

Nubble Lighthouse

Nubble Lighthouse

If you’re searching for Instagrammable photos on your voyage north, you’ll want to stop at Nubble Lighthouse in York. The iconic light is considered the most photographed lighthouse on the East Coast, and for a good reason—Cape Neddick is classic New England. The crashing Atlantic waves on the rocky coast, the Victorian-style, red-roofed light keeper’s house, and the vividly green grass covering the hills of the island combine for a stunning welcome into coastal Maine.

Take U.S. Route 1

Once you make it through Portsmouth, it’s smooth sailing to your home away from home in the Kennebunks. So what’s the rush? After all, this is a vacation to unwind. Get off noisy I-95 and onto the A1A of New England.

U.S. Route 1 parallels I-95 the entire drive from Boston, so hop on whenever you’re ready to get away from the fast-paced flow. There’s no need to get rerouted when you travel north on Route 1—the two-lane highway whizzes past most of the coast’s iconic sights, including picturesque New England lighthouses and bustling lobstermen at work. Quiet Kennebunkport is just a short eight miles off of Route 1.

End Your Road Trip at The Inn at English Meadows

serenity room inn at english meadows

After your road trip from Boston to Kennebunkport, cozy up by a gas fireplace underneath your down duvet. Each morning, enjoy the inn’s exclusively brewed coffee and indulge in a decadent three-course, chef-inspired breakfast. All entrees are prepared with the freshest, seasonal produce and are made in-house. Our inn provides your picture-perfect New England escape in Kennebunk.

Get on the road and start planning your trip to Coastal Maine. Check our availability today!

There is so much more to Explore!

Discover all there is to do in Kennebunkport, Maine.


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