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20 Oct 2025
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7 day New England Road Trip Itinerary

7-Day New England Road Trip Itinerary Overview

Embark on an unforgettable 7-day road trip through New England, where rich history, diverse landscapes, and charming coastal towns await. Your journey begins in Boston, tracing the storied past along the iconic Freedom Trail, with must-see stops like Boston Common and Paul Revere’s House. Next, explore the historic halls and vibrant atmosphere of Harvard University in Cambridge. Heading north, marvel at the captivating views of Portland Head Light, Maine’s most photographed lighthouse. Relish the majestic beauty and outdoor activities of Acadia National Park, where rugged mountains meet the Atlantic. The adventure continues in New Hampshire’s White Mountains, renowned for breathtaking summits and woodland tranquility. Journey to western Massachusetts to immerse yourself in literary history at The Mount, Edith Wharton’s Home, surrounded by beautiful gardens and architectural elegance. The trip concludes along Rhode Island’s famed Newport Cliff Walk, where dramatic ocean vistas and historic mansions line a scenic trail, leaving you with enduring memories of New England’s quintessential charm.


Recommended Activities

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    Freedom Trail

    The Freedom Trail offers an immersive journey through American history with 16 significant sites related to the nation's founding, making it a must-see for history enthusiasts.
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    Harvard University

    Visiting Harvard University lets you explore the oldest university in the United States, admire beautiful architecture, and absorb the scholarly atmosphere of Cambridge.
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    Minute Man National Historical Park

    Key Revolutionary War site and walking trails
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    The Mount, Edith Wharton’s Home

    The Mount provides insight into the life and work of Pulitzer Prize-winning author Edith Wharton, set in stunning Gilded Age gardens and a beautifully preserved mansion.
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    Green Mountains National Forest

    Beautiful hikes and quintessential Vermont scenery
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    Shaker Village of Canterbury

    Historic site with Shaker heritage and crafts
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    White Mountains

    The White Mountains offer breathtaking mountain scenery, hiking trails, waterfalls, and opportunities for outdoor adventure throughout the year.
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    Portland Head Light

    Portland Head Light is an iconic New England lighthouse with stunning ocean views, historical significance, and picturesque surroundings in Fort Williams Park.
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    Acadia National Park

    Acadia National Park features dramatic coastal landscapes, forested mountains, and diverse wildlife, making it ideal for hiking, biking, and scenic drives.
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    Martha's Vineyard

    Charming island with beaches and quaint towns
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    Gillette Castle State Park

    Unique medieval-style castle and scenic park
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    Mark Twain House & Museum

    Historic home of the famous American author
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    Mystic Seaport Museum

    Leading maritime museum with historic ships
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    Newport Cliff Walk

    Newport Cliff Walk offers a unique combination of scenic ocean views and historic Gilded Age mansions along a picturesque coastal trail.
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Restaurants

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    Eventide Oyster Co. - Portland, ME

    4.5
    $$$$

    Eventide Oyster Co. - Portland, ME

    Famed for its creative seafood dishes and fresh oysters, this Portland staple reflects the essence of Maine's coastal cuisine.
    4.5
    $$$$
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    Neptune Oyster

    9
    $$$$

    Neptune Oyster

    A Boston icon, known for its legendary lobster rolls and pristine seafood in a cozy North End setting.
    9
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    Hen of the Wood, Burlington, Vermont

    4.7
    $$$$

    Hen of the Wood, Burlington, Vermont

    Celebrated for its farm-to-table approach, this Vermont restaurant highlights the best of local ingredients and seasonal menus.
    4.7
    $$$$
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    Frank Pepe Pizzeria Napoletana

    4.6
    $$$$

    Frank Pepe Pizzeria Napoletana

    A New Haven institution, famed for its coal-fired pizzas, especially the white clam pie, making it a must-visit for pizza lovers.
    4.6
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    The Mooring Seafood Kitchen & Bar

    4.3
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    The Mooring Seafood Kitchen & Bar

    A Newport favorite for classic New England seafood and gorgeous waterfront views.
    4.3
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Hotels

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    The Lenox Hotel

    9.1

    The Lenox Hotel

    A historic luxury hotel in Boston’s Back Bay, offering elegant rooms and convenient access to major attractions.
    9.1
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    Portland Harbor Hotel

    Portland Harbor Hotel

    A top-rated boutique hotel centrally located in Portland’s Old Port, known for its comfort and hospitality.
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    Bar Harbor Inn & Spa

    4.6

    Bar Harbor Inn & Spa

    Overlooking Frenchman Bay, this iconic hotel is perfect for visiting Acadia National Park and enjoying serene coastal views.
    4.6
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    Omni Mount Washington Resort

    8.6

    Omni Mount Washington Resort

    This grand resort in the White Mountains features breathtaking views, historic charm, and outdoor activities year-round.
    8.6
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    Castle Hill Inn

    4.5

    Castle Hill Inn

    A luxurious oceanfront retreat in Newport, offering New England elegance and stunning views of Narragansett Bay.
    4.5
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Local Events & Happenings

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    Snarky Puppy

    Snarky Puppy

    The event will take place at Groton Hill Music Center in Groton.
    Map IconGroton Hill Music Center in Groton (6.2 mi)
    Calendar Icon19 Apr 2026
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    John Cleese

    John Cleese

    The event will take place at Lowell Memorial Auditorium in Lowell.
    Map IconLowell Memorial Auditorium in Lowell (7.56 mi)
    Calendar Icon23 Oct 2025
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    Walker Hayes: Unplugged

    Walker Hayes: Unplugged

    The event will take place at Lowell Memorial Auditorium in Lowell.
    Map IconLowell Memorial Auditorium in Lowell (7.56 mi)
    Calendar Icon22 Nov 2025
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    Blippi: Join The Band

    Blippi: Join The Band

    The event will take place at Lowell Memorial Auditorium in Lowell.
    Map IconLowell Memorial Auditorium in Lowell (7.56 mi)
    Calendar Icon3 Dec 2025
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    Vienna Boys' Choir

    Vienna Boys' Choir

    The event will take place at Lowell Memorial Auditorium in Lowell.
    Map IconLowell Memorial Auditorium in Lowell (7.56 mi)
    Calendar Icon6 Dec 2025
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    Cirque Musica

    Cirque Musica

    The event will take place at Lowell Memorial Auditorium in Lowell.
    Map IconLowell Memorial Auditorium in Lowell (7.56 mi)
    Calendar Icon11 Dec 2025
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    Chris Young

    Chris Young

    The event will take place at Lowell Memorial Auditorium in Lowell.
    Map IconLowell Memorial Auditorium in Lowell (7.56 mi)
    Calendar Icon13 Dec 2025
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Travel Gems from Reddit

  • Reddit Icon

    142 votes, 323 comments. I would appreciate your feedback on a New England road trip my cousin and I are planning for next fall. Its ambitious but

    Your advice on my planned New England trip

    142 votes, 323 comments. I would appreciate your feedback on a New England road trip my cousin and I are planning for next fall. Its ambitious but

    /r/roadtrip
  • Reddit Icon

    Hi everyone. We're flying in to Boston in early June, renting a car, and driving to Bar Harbor, Maine. Then planning on going through Vermont and New

    New England road trip ideas

    Hi everyone. We're flying in to Boston in early June, renting a car, and driving to Bar Harbor, Maine. Then planning on going through Vermont and New

    /r/roadtrip
  • Reddit Icon

    New England road trip Hello! We are a couple from the Netherlands (Both 31), and we're planning a road trip from NYC through New England up to Maine. Or perhaps mostly Vermont...

    New England road trip

    New England road trip Hello! We are a couple from the Netherlands (Both 31), and we're planning a road trip from NYC through New England up to Maine. Or perhaps mostly Vermont...

    /r/newengland
  • Reddit Icon

    I just updated our itinerary to include route 1. ... Saw the map and was going to suggest the same. My first trip to Acadia we drove up the coast from Mass. It was late August...

    7 Days in New England - Looking for Suggestions

    I just updated our itinerary to include route 1. ... Saw the map and was going to suggest the same. My first trip to Acadia we drove up the coast from Mass. It was late August...

    /r/newengland
  • Reddit Icon

    (theres an edit/update at the bottom) Hey all I'm looking for some help planning a trip at the end of the year around New England. I'll be visiting

    Recommendations for road trip around New England

    (theres an edit/update at the bottom) Hey all I'm looking for some help planning a trip at the end of the year around New England. I'll be visiting

    /r/roadtrip

Music for Your Journey

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    Red Hot Chili Peppers - Road Trippin'

    Red Hot Chili Peppers - Road Trippin'

    A mellow, reflective song perfect for scenic drives and open roads.
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    Eagles - Take It Easy - 2013 Remaster

    Eagles - Take It Easy - 2013 Remaster

    A classic, feel-good anthem that captures the spirit of adventure and exploration.
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    Neil Diamond - Sweet Caroline

    Neil Diamond - Sweet Caroline

    An upbeat, sing-along favorite that pays homage to Massachusetts and lifts the mood.
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    Don McLean - American Pie

    Don McLean - American Pie

    An evocative song celebrating travel and wonder, fitting for discovering new places.
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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    The ultimate road trip anthem that energizes any journey and keeps spirits high.
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    Woody Guthrie - This Land is Your Land

    Woody Guthrie - This Land is Your Land

    A folk classic that encapsulates the diverse beauty and freedom of America.
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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    A heartwarming tune about belonging and finding comfort on the road.
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    Led Zeppelin - Going to California - Remaster

    Led Zeppelin - Going to California - Remaster

    A dreamy, reflective song well-suited for driving through diverse landscapes.
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    The Innocence Mission - Happy Birthday

    The Innocence Mission - Happy Birthday

    A cheerful local tune perfect for exploring New England's natural wonders.
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    Noah Kahan - Maine

    Noah Kahan - Maine

    A soothing homage that beautifully captures the essence of Maine’s scenery.
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