Maine

2024-09-04

Edit

Save

Boston to Maine Road Trip Itinerary

Boston to Maine Scenic Route Road Trip Overview

Embark on a memorable road trip from Boston to Maine, covering some of New England's most picturesque and historically rich locations. Start your journey in the vibrant city of Boston, renowned for its integral role in American history, academic landmarks, and bustling urban atmosphere. Next, travel to Salem, where the echoes of the infamous 1692 witch trials provide a unique historical backdrop, accompanied by charming streets and a scenic waterfront.

Continue your journey to Portsmouth, a quaint coastal town that offers a blend of colonial charm and maritime heritage, perfect for leisurely exploration and delightful seafood dining. From there, head to Ogunquit, where breathtaking beaches, the idyllic Marginal Way cliff walk, and an inviting arts scene await.

Next, visit Kennebunkport, a picturesque seaside village known for its historic homes, beautiful coastline, and exceptional waterfront dining experiences. Your adventure continues to the lively city of Portland, boasting a vibrant arts district, historic Old Port, and an array of culinary delights set against scenic coastal views.

As you venture further, stop in Freeport, famed for its flagship L.L.Bean store and numerous outlet shops, as well as access to natural treasures like Wolfe's Neck Woods State Park. Conclude your trip in Brunswick, a charming town with a rich maritime past, home to Bowdoin College, and offering cultural attractions like the Bowdoin College Museum of Art. This road trip promises a blend of history, culture, and stunning New England landscapes.

Plan your dream trip for Free with AI

Create a personalized itinerary effortlessly with our AI-powered planner.

Recommended Explorations

1
Boston
Remove Edit Reorder
Rich in American history with landmarks like the Freedom Trail, vibrant neighborhoods, and a strong academic presence with prestigious universities.
2
Salem
Remove Edit Reorder
Known for its 1692 witch trials, Salem offers a unique historical experience along with museums, historic sites, and a charming waterfront.
3
Portsmouth
Remove Edit Reorder
A picturesque coastal town with a blend of Colonial and maritime history, scenic views, boutique shopping, and excellent seafood restaurants.
4
Ogunquit
Remove Edit Reorder
A beautiful coastal town known for its stunning beaches, the Marginal Way scenic cliff walk, and a vibrant arts scene with galleries and theaters.
5
Kennebunkport
Remove Edit Reorder
A charming seaside village famous for its historic architecture, maritime museums, and as a summer haven with lovely beaches and waterfront dining.
6
Portland
Remove Edit Reorder
A lively city with a thriving arts district, historic Old Port waterfront, excellent dining options, and a variety of outdoor activities including nearby parks and lighthouses.
7
Freeport
Remove Edit Reorder
Home to the flagship L.L.Bean store and numerous outlet shops, Freeport offers great shopping, as well as access to beautiful natural areas like Wolfe's Neck Woods State Park.
8
Brunswick
Remove Edit Reorder
A charming town with a rich maritime history, home to Bowdoin College, and offering cultural attractions like the Bowdoin College Museum of Art and the scenic Androscoggin River.

Local Events & Happenings

Music for Your Journey

Tasty Picks

Stay Recommendations

The Liberty, a Luxury Collection Hotel, Boston, Massachusetts
The Liberty, a Luxury Collection Hotel, Boston, Massachusetts
A former jail turned luxury hotel in Boston, offering unique historical features blended with modern amenities.
The Salem Inn, Salem
The Salem Inn, Salem
Comprised of three historic homes in Salem, this charming inn offers a cozy, historic ambiance with modern comforts, perfect for history buffs.
The Hotel Portsmouth
8.5
The Hotel Portsmouth
A boutique hotel in a beautifully restored Victorian mansion in Portsmouth, offering a blend of old-world charm and modern conveniences.
8.5
Visit Website
The Cliff House Maine
4.6
The Cliff House Maine
Perched on the cliffs of Ogunquit, this luxurious resort offers stunning ocean views and top-notch amenities, ideal for a scenic retreat.
4.6
The Press Hotel, Maine
4.7
The Press Hotel, Maine
Located in the former headquarters of the Portland Press Herald, this unique hotel in Portland combines journalism-themed design with contemporary luxury.
4.7