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16 Mar 2025Updated last time
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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.


Recommended Activities

  • Rich in American history with landmarks like the Freedom Trail, vibrant neighborhoods, and a strong academic presence with prestigious universities.
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  • Known for its 1692 witch trials, Salem offers a unique historical experience along with museums, historic sites, and a charming waterfront.
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  • A picturesque coastal town with a blend of Colonial and maritime history, scenic views, boutique shopping, and excellent seafood restaurants.
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  • A beautiful coastal town known for its stunning beaches, the Marginal Way scenic cliff walk, and a vibrant arts scene with galleries and theaters.
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    Kennebunkport

    A charming seaside village famous for its historic architecture, maritime museums, and as a summer haven with lovely beaches and waterfront dining.
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  • 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.
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  • 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.
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  • 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.
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Restaurants

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    The Barking Crab

    4.1
    $$$$

    The Barking Crab

    A lively seafood shack on the Boston waterfront known for its fresh lobster and casual, fun atmosphere.
    4.1
    $$$$
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    Turner's Seafood at Lyceum Hall

    4.6
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    Turner's Seafood at Lyceum Hall

    Located in Salem, this historic venue serves fresh, locally-sourced seafood in a beautifully restored building.
    4.6
    $$$$
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    Jumpin' Jay's Fish Cafe

    4.2
    $$$$

    Jumpin' Jay's Fish Cafe

    A modern seafood restaurant in Portsmouth praised for its creative dishes and fresh ingredients.
    4.2
    $$$$
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    The Front Porch Piano Bar and Restaurant

    4.5
    $$$$

    The Front Porch Piano Bar and Restaurant

    In Ogunquit, this spot offers great food and live piano music, making for a unique and entertaining dining experience.
    4.5
    $$$$
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    The Lost Kitchen

    4.8
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    The Lost Kitchen

    An exclusive dining experience in Freedom, Maine, where the seasonal menu and stunning rural setting create an unforgettable meal.
    4.8
    $$$$
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Hotels

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    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.
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    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.
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    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
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    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
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    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
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Local Events & Happenings

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    Deathtrap

    Deathtrap

    The event will take place at Biddeford City Theater in Biddeford.
    Map IconBiddeford City Theater in Biddeford (16.68 mi)
    Calendar Icon10 Oct 2025
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    A Swinging Christmas: The Holiday Music of Tony Bennett

    A Swinging Christmas: The Holiday Music of Tony Bennett

    The event will take place at Biddeford City Theater in Biddeford.
    Map IconBiddeford City Theater in Biddeford (16.68 mi)
    Calendar Icon6 Dec 2025
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    The Secret Garden

    The Secret Garden

    The event will take place at Biddeford City Theater in Biddeford.
    Map IconBiddeford City Theater in Biddeford (16.68 mi)
    Calendar Icon13 Mar 2026
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Travel Gems from Reddit


Music for Your Journey

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    Don McLean - American Pie

    Don McLean - American Pie

    A classic road trip anthem that captures the nostalgia and spirit of Americana.
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    An upbeat, driving tune that perfectly sets the mood for hitting the open road.
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    Neil Diamond - Sweet Caroline

    Neil Diamond - Sweet Caroline

    A beloved song that will get everyone singing along, especially fitting as a nod to Boston.
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A laid-back track that encourages travelers to enjoy the journey and take things in stride.
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    An essential road trip song celebrating the joy of travel and new experiences.
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    Woody Guthrie - This Land is Your Land

    Woody Guthrie - This Land is Your Land

    A folk classic that highlights the beauty and diversity of the American landscape.
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    Journey - Don't Stop Believin'

    Journey - Don't Stop Believin'

    An iconic anthem of perseverance and hope, great for keeping spirits high on long drives.
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    Edith Whiskers - Home

    Edith Whiskers - Home

    A feel-good song that captures the comfort of being on the journey back home.
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    Bruce Springsteen - Born to Run

    Bruce Springsteen - Born to Run

    An exhilarating rock anthem celebrating the freedom and adventure of the open road.
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    A classic tune about independence and forging one's own path, fitting for a road trip.
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