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15 Aug 2025
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Nashua, NH to Portland, ME Road Trip Itinerary

Nashua, NH to Portland, ME Road Trip Overview

Embark on a captivating journey from Nashua, NH to Portland, ME, experiencing the best of New England along the way. Start in Nashua, a city known for its quaint downtown and riverside charm, then indulge in shopping at Merrimack Premium Outlets. Dive into culture and history in bustling Manchester before tracing the literary footsteps of Robert Frost at his state historic site. Explore Concord, New Hampshire’s historic capital, and meander through the charming seaport of Portsmouth, filled with boutiques and coastal views. Continue your adventure at Fort McClary State Historic Site in Maine, offering both historic intrigue and panoramic river vistas. Shopping enthusiasts will love the Kittery Outlets’ name-brand deals. Relax and unwind at Old Orchard Beach, a vibrant seaside locale perfect for fun and leisure. Conclude your road trip in picturesque Portland, ME, where a thriving culinary scene, historic sites, and the iconic waterfront await, ensuring a memorable and enriching road trip experience.


Recommended Activities

  • Nashua offers a charming downtown with vibrant shops, dining, and scenic river views. It's a great starting point for exploring southern New Hampshire.
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    Merrimack Premium Outlets

    This outlet mall is perfect for shopping enthusiasts, featuring a wide variety of top-brand stores, deals, and a convenient pit stop for travel necessities.
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    Manchester, NH

    Manchester is New Hampshire’s largest city, known for its dynamic arts scene, historic mill district, unique museums, and excellent breweries.
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    Robert Frost Farm State Historic Site

    This historic site honors the famous poet Robert Frost, offering guided tours, picturesque trails, and insights into his literary legacy in a tranquil rural setting.
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    Concord, NH

    As New Hampshire’s capital, Concord boasts rich history, a vibrant downtown, local shops, cafes, and attractions like the New Hampshire State House.
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    Portsmouth, NH

    Portsmouth is a historic seaport with charming streets, unique shops, waterfront restaurants, and colonial-era sites, making it a must-visit for history and culture lovers.
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    Fort McClary State Historic Site

    This site features a well-preserved 19th-century fort, offering fascinating local history, guided tours, and beautiful views of the Piscataqua River.
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    Kittery Outlets

    A premier shopping destination with a wide variety of name-brand stores and great deals, perfect for bargain hunters and those looking to take a shopping break along the route.
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    Old Orchard Beach

    A classic New England beach town known for its sandy shoreline, lively pier, amusement parks, and vibrant summer atmosphere, making it an ideal spot to relax and have fun.
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    Portland, ME

    Portland is famous for its vibrant food scene, historic Old Port district, picturesque waterfront, and cultural attractions such as museums, galleries, and lighthouses, making it a lively and memorable destination.
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Restaurants

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    The Red Arrow Diner

    The Red Arrow Diner

    A quirky and historic 24-hour diner famous for its comfort food and celebrity wall, offering a true taste of New Hampshire in a fun atmosphere.
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    The Friendly Toast - Portsmouth, NH

    The Friendly Toast - Portsmouth, NH

    Known for its eclectic decor and inventive menu, The Friendly Toast in Portsmouth is a must-visit for breakfast lovers and those seeking a unique dining experience.
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    When Pigs Fly Wood-Fired Pizzeria

    4.5
    $$$$

    When Pigs Fly Wood-Fired Pizzeria

    This Kittery hotspot serves creative pizzas with fresh ingredients in a rustic, wood-fired oven setting that’s both cozy and unusual.
    4.5
    $$$$
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    Palace Diner

    4.6
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    Palace Diner

    Located in an original 1927 railcar in Biddeford, Palace Diner offers a retro vibe and delicious classic American fare with a twist.
    4.6
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    The Holy Donut

    4.5
    $$$$

    The Holy Donut

    A Portland favorite, this spot specializes in unique potato-based donuts in a variety of unexpected flavors, making it a tasty and memorable stop.
    4.5
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Hotels

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    Ash Street Inn

    4.9

    Ash Street Inn

    A charming Victorian bed-and-breakfast in Manchester, offering unique character, personalized touches, and gourmet breakfast in a historic setting.
    4.9
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    Ale House Inn

    4.3

    Ale House Inn

    This boutique hotel in Portsmouth is set within a historic brewery warehouse, blending industrial chic design with modern comforts in the heart of downtown.
    4.3
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    The Water Street Inn

    4.9

    The Water Street Inn

    Nestled by the river in Kittery, this cozy boutique inn features whimsical decor and easy access to downtown shops and restaurants.
    4.9
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    The Press Hotel

    9.5

    The Press Hotel

    Located in Portland in the former home of the Portland Press Herald, this art-filled boutique hotel captures the spirit of journalism and the city’s creative flare.
    9.5
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    Inn By The Sea

    4.7

    Inn By The Sea

    Situated on the coast near Portland, this eco-luxury resort features beach access, contemporary suites, and environmentally friendly practices for a unique and relaxing stay.
    4.7
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Local Events & Happenings

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    Brian Culbertson

    Brian Culbertson

    The event will take place at The Music Hall-NH in Portsmouth.
    Map IconThe Music Hall-NH in Portsmouth (10.99 mi)
    Calendar Icon21 Oct 2025
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    Willy Wonka and The Chocolate Factory The Taste-A-Long Experience

    Willy Wonka and The Chocolate Factory The Taste-A-Long Experience

    The event will take place at The Music Hall-NH in Portsmouth.
    Map IconThe Music Hall-NH in Portsmouth (10.99 mi)
    Calendar Icon23 Oct 2025
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    Autechre w/ Mark Broom

    Autechre w/ Mark Broom

    The event will take place at 3S Artspace in Portsmouth.
    Map Icon3S Artspace in Portsmouth (10.99 mi)
    Calendar Icon29 Oct 2025
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    David Brighton

    David Brighton

    The event will take place at The Music Hall-NH in Portsmouth.
    Map IconThe Music Hall-NH in Portsmouth (10.99 mi)
    Calendar Icon1 Nov 2025
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    Natalie Merchant

    Natalie Merchant

    The event will take place at The Music Hall-NH in Portsmouth.
    Map IconThe Music Hall-NH in Portsmouth (10.99 mi)
    Calendar Icon12 Nov 2025
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    Randy Rainbow

    Randy Rainbow

    The event will take place at The Music Hall-NH in Portsmouth.
    Map IconThe Music Hall-NH in Portsmouth (10.99 mi)
    Calendar Icon17 Nov 2025
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    Menopause The Musical 2

    Menopause The Musical 2

    The event will take place at The Music Hall-NH in Portsmouth.
    Map IconThe Music Hall-NH in Portsmouth (10.99 mi)
    Calendar Icon19 Apr 2026
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Travel Gems from Reddit

  • Reddit Icon

    So I am planning a New England road trip Oct 8-17 with specific places and states I want to see/stay in. I have about one week to try to hit up the

    New England Road Trip Help/Suggestions

    So I am planning a New England road trip Oct 8-17 with specific places and states I want to see/stay in. I have about one week to try to hit up the

    /r/newengland
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    Planning a ~10 day road trip with our dog in September. We live in the South and are not too familiar with Maine/New Hampshire area. We will have our

    Maine/New Hampshire Road Trip

    Planning a ~10 day road trip with our dog in September. We live in the South and are not too familiar with Maine/New Hampshire area. We will have our

    /r/newengland
  • Reddit Icon

    I'm going on a road trip from Ohio to Portland, Maine next weekend and I'd like to stop and see/do something in every state on the way. What should I

    What should I see in Southern New Hampshire?

    I'm going on a road trip from Ohio to Portland, Maine next weekend and I'd like to stop and see/do something in every state on the way. What should I

    /r/newhampshire

Music for Your Journey

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    Rascal Flatts - Life is a Highway

    Rascal Flatts - Life is a Highway

    A classic road trip anthem that energizes any drive with its upbeat tempo and lyrics about adventure.
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    WALK THE MOON - Shut Up and Dance

    WALK THE MOON - Shut Up and Dance

    This catchy pop-rock track brings high spirits and fun, perfect for cruising along open roads.
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    Rusted Root - Send Me on My Way

    Rusted Root - Send Me on My Way

    An uplifting and whimsical tune that creates a sense of joyful travel and exploration.
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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    A feel-good, folksy song about finding comfort on a journey, ideal for scenic landscapes.
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    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Fleetwood Mac - Go Your Own Way - 2004 Remaster

    Classic rock song about independence and moving forward, fitting for a trip on the open highway.
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    Ed Sheeran - Shivers

    Ed Sheeran - Shivers

    A vibrant, modern pop song that keeps energy high and spirits up during long stretches.
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    George Ezra - Budapest

    George Ezra - Budapest

    Indie folk rhythm and storytelling lyrics make this song a travel favorite.
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    John Denver - Take Me Home, Country Roads

    John Denver - Take Me Home, Country Roads

    A nostalgic song that celebrates the beauty of rural roads and the open country.
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    Edward Sharpe & The Magnetic Zeros - Home

    Edward Sharpe & The Magnetic Zeros - Home

    Smooth vocals and a rolling beat evoke the feeling of returning home after a long adventure.
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    Willie Nelson - On The Road Again - Live

    Willie Nelson - On The Road Again - Live

    A true road trip classic about the joy of being on the move and experiencing new places.
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