New Hampshire

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

1
Nashua, NH
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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
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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
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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
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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
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As New Hampshire’s capital, Concord boasts rich history, a vibrant downtown, local shops, cafes, and attractions like the New Hampshire State House.
6
Portsmouth, NH
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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
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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
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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
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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
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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

The Red Arrow Diner
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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.
The Friendly Toast - Portsmouth, NH
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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.
When Pigs Fly Wood-Fired Pizzeria
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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
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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
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4.5
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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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Stay Recommendations

Ash Street Inn
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Ash Street Inn
A charming Victorian bed-and-breakfast in Manchester, offering unique character, personalized touches, and gourmet breakfast in a historic setting.
Ale House Inn
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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.
The Water Street Inn
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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.
The Press Hotel
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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
Inn By The Sea
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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

Local Events & Happenings

Itzhak Perlman
Itzhak Perlman
The event will take place at The Music Hall-NH in Portsmouth.
The Music Hall-NH in Portsmouth (11.3 mi)
20 Sep 2025
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Autechre w/ Mark Broom
Autechre w/ Mark Broom
The event will take place at 3S Artspace in Portsmouth.
3S Artspace in Portsmouth (11.3 mi)
29 Oct 2025
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Natalie Merchant
Natalie Merchant
The event will take place at The Music Hall-NH in Portsmouth.
The Music Hall-NH in Portsmouth (11.3 mi)
12 Nov 2025
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Sue Foley Livestream Event from Jimmys Jazz and Blues Club
Sue Foley Livestream Event from Jimmys Jazz and Blues Club
The event will take place at Jimmy's Jazz and Blues Club in Portsmouth.
Jimmy's Jazz and Blues Club in Portsmouth (13.13 mi)
15 Aug 2025
Visit Website
Sue Foley
Sue Foley
Fresh off a double win at the 2025 Blues Music Awards and a GRAMMY® nomination for One Guitar Woman, Sue Foley brings over 35 years of powerhouse guitar work and fiery Texas blues back to the stage. Known for her commanding presence and signature pin...
Jimmy's Jazz and Blues Club in Portsmouth (13.13 mi)
15 Aug 2025
Visit Website
Gary Hoey Livestream from Jimmy's Jazz and Blues Club
Gary Hoey Livestream from Jimmy's Jazz and Blues Club
The event will take place at Jimmy's Jazz and Blues Club in Portsmouth.
Jimmy's Jazz and Blues Club in Portsmouth (13.13 mi)
17 Aug 2025
Visit Website
Gary Hoey: Avalanche Tour
Gary Hoey: Avalanche Tour
Listed as one of the top 100 guitarists of all time, Gary Hoey has built a legendary career with 22 albums and collaborations with rock icons. His breakout came in 1992 with a Billboard Top 5 hit, Hocus Pocus. Hoey's distinct guitar mastery and fiery...
Jimmy's Jazz and Blues Club in Portsmouth (13.13 mi)
17 Aug 2025
Visit Website