Nashua, NH to Portland, ME Road Trip Itinerary

09 Jun 2026Updated last time

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.
  • 2

    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.
  • 3

    Manchester, NH

    Manchester is New Hampshire’s largest city, known for its dynamic arts scene, historic mill district, unique museums, and excellent breweries.
  • 4

    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.
  • 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.
  • 7

    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.
  • 8

    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.
  • 9

    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.
  • 10

    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.

Restaurants

  • Picture for The Red Arrow Diner

    The Red Arrow Diner

    61 Lowell St, Manchester, NH 03101, United States
    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.
  • Picture for The Friendly Toast - Portsmouth, NH

    The Friendly Toast - Portsmouth, NH

    113 Congress Street, Portsmouth, NH 03801, United States
    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.
  • Picture for When Pigs Fly Wood-Fired Pizzeria

    When Pigs Fly Wood-Fired Pizzeria

    460 U.S. Rte 1, Kittery, ME 03904, USA
    This Kittery hotspot serves creative pizzas with fresh ingredients in a rustic, wood-fired oven setting that’s both cozy and unusual.
    4.5
    $$$$
  • Picture for Palace Diner
    18 Franklin St, Biddeford, ME 04005, United States
    Located in an original 1927 railcar in Biddeford, Palace Diner offers a retro vibe and delicious classic American fare with a twist.
    4.6
    $$$$
  • Picture for The Holy Donut

    The Holy Donut

    194 Park Ave, Portland, ME 04102, United States
    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
    $$$$

Hotels

  • Ash Street Inn

    118 Ash St, Manchester, NH 03104, USA

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

    121 Bow St, Portsmouth, NH 03801, USA

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

    6 Water St, Kittery, ME 03904, USA

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

    119 Exchange St, Portland, ME 04101, United States

    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.
  • Inn By The Sea

    40 Bowery Beach Rd, Cape Elizabeth, ME 04107, ארצות הברית

    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.

Local Events & Happenings

  • Picture for Matt Fraser - Ages: 18+

    Matt Fraser - Ages: 18+

    The Music Hall-NH in Portsmouth (10.99 mi)28 May 2026
    The event will take place at The Music Hall-NH in Portsmouth.
  • Picture for The Pout-Pout Fish

    The Pout-Pout Fish

    The Music Hall-NH in Portsmouth (10.99 mi)29 May 2026
    The event will take place at The Music Hall-NH in Portsmouth.
  • Picture for Portsmouth Symphony Orchestra

    Portsmouth Symphony Orchestra

    The Music Hall-NH in Portsmouth (10.99 mi)31 May 2026
    The event will take place at The Music Hall-NH in Portsmouth.
  • Picture for Blippi: Be Like Blippi Tour

    Blippi: Be Like Blippi Tour

    The Music Hall-NH in Portsmouth (10.99 mi)2 Jun 2026
    The event will take place at The Music Hall-NH in Portsmouth.
  • Picture for The Moth

    The Moth

    The Music Hall-NH in Portsmouth (10.99 mi)5 Jun 2026
    The event will take place at The Music Hall-NH in Portsmouth.
  • Picture for Jenna Bush Hager

    Jenna Bush Hager

    The Music Hall-NH in Portsmouth (10.99 mi)11 Jun 2026
    The event will take place at The Music Hall-NH in Portsmouth.
  • Picture for A Conversation with Dr. Temple Grandin

    A Conversation with Dr. Temple Grandin

    The Music Hall-NH in Portsmouth (10.99 mi)12 Jun 2026
    The event will take place at The Music Hall-NH in Portsmouth.

Travel Gems from Reddit

  • New England Road Trip Help/Suggestions

    /r/newengland

    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

  • Maine/New Hampshire Road Trip

    /r/newengland

    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

  • What should I see in Southern New Hampshire?

    /r/newhampshire

    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