
Set out on a coastal road trip from Boston to Bar Harbor and experience the best of New England’s shoreline. Along the way, you’ll discover historic towns, breathtaking views, and some of the freshest seafood around. Each of the following 15 stops offers something unique: a scenic hike, a charming harbor, or a piece of local history awaiting your arrival.
Boston, Massachusetts

Your journey begins in the heart of Boston, where history and modernity meet. Before hitting the open road, explore Boston Common, visit the Freedom Trail, or grab a bite at Quincy Market. Boston’s vibrant atmosphere is the perfect starting point for your coastal adventure, setting the tone for what’s to come.
Salem, Massachusetts

Known for its witch trials, Salem offers a fascinating glimpse into New England’s spooky history. Wander through the Salem Witch Museum, stroll the historic streets, and embrace the town’s quirky, mystical vibe. It’s a small town packed with personality and a must-stop on your way north.
Cape Ann, Massachusetts

A short detour to Cape Ann brings you to the picturesque towns of Gloucester and Rockport. Famous for their artistic communities and working harbors, you can enjoy local art galleries, fresh seafood, and stunning coastal views. Don’t miss the iconic Motif No. 1, a popular spot for artists and photographers.
Newburyport, Massachusetts

This is a perfect place for a quick stop with charming seaside vibes. Stroll along the Merrimack River, explore and buy at local boutiques, or grab a coffee in Market Square. Newburyport’s historic architecture and cozy, small-town charm make it a great place to stretch your legs and take in the local scene.
Portsmouth, New Hampshire

Crossing into New Hampshire, Portsmouth offers a lively downtown packed with a historical, cultural, and educational coastal charm. Visit the Strawbery Banke Museum and walk along the waterfront to discover the many harborfront restaurants offering delicious fresh seafood. Old-school charm with modern comforts together in a perfect mix.
Ogunquit, Maine

Ogunquit is a picturesque stop for relaxation and stunning views. This location is famous for its three-mile-long sandy beach. The peaceful seaside ambiance makes it an ideal spot for a mid-trip break, where you can walk along the Marginal Way or visit Perkins Cove for quaint shops and art galleries.
Kennebunkport, Maine

Home to the famous Bush family compound, Kennebunkport offers a charming mix of things to do that appeal to history, shopping, and outdoor activities buffs. Explore Dock Square for boutique shopping, and be sure to grab a lobster roll for an authentic Maine experience.
Portland, Maine

As Maine’s largest city, Portland is a culture and history hub. Visit the Old Port district, filled with cobblestone streets and 19th-century buildings, or climb to the top of the Portland Observatory for sweeping views. Don’t miss Portland’s thriving food scene, particularly its seafood dishes.
Freeport, Maine

Home to the famous L.L. Bean flagship store, Freeport is a shopping destination with a charming small-town feel. In addition to its outlet stores, you can explore nearby Wolfe’s Neck Woods State Park for scenic hiking trails. This town offers the perfect balance of retail therapy and nature exploration.
Brunswick, Maine

Brunswick is home to Bowdoin College, which has a lot of cultural activities, such as museums, theaters, and galleries. It’s a quiet yet vibrant stop along your journey. Stroll through the campus, visit the Bowdoin College Museum of Art, or enjoy a picnic in one of its many parks.
Boothbay Harbor, Maine

This coastal town is known for its stunning harbor views and maritime history. Take a boat tour to see the islands, visit the Coastal Maine Botanical Gardens, or stroll through the local shops. Boothbay Harbor offers a tranquil yet engaging experience for travelers seeking a connection with the ocean.
Camden, Maine

Between the mountains and the sea, Camden offers some of the most breathtaking views on the Maine coast. Love outdoor adventures? Then stop in this city. Here, you can hike up Mount Battie for panoramic views of the harbor or take a sailboat ride to explore the coastline.
Belfast, Maine

When you get to this destination, you can wander through galleries, dine at farm-to-table restaurants, or walk along the harborfront. This artsy town has a vibrant waterfront and a thriving local art scene that offers a relaxing and culturally rich stop before heading further north along the coast.
Ellsworth, Maine

The perfect pit stop before reaching your final destination. As the gateway to Acadia National Park, Ellsworth is a convenient stop to stock up on supplies or explore local attractions. Visit the Woodlawn Museum, shop in the historic downtown, or grab a bite at one of the many eateries.
Bar Harbor, Maine

Your road trip culminates in Bar Harbor, a charming town at the edge of Acadia National Park. Bar Harbor’s mix of nature, dining, and history offers the perfect ending to your journey. Explore the stunning park with hikes up Cadillac Mountain, or enjoy the breathtaking coastal views.