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Charming New England Road Trip: Cold Spring to Portsmouth & Kittery with Family Fun

Viewed by 75 travelers

Day 1: Travel & Explore Portsmouth

Cold Spring, NY to Portsmouth, NH on September 24, 2025

7:00am

Breakfast at Cold Spring Pizza

Start your day with a delicious breakfast pizza or pastries at a local favorite in Cold Spring to fuel up for the trip.
USD15, 0h45m

8:00am

Drive from Cold Spring to Portsmouth

Enjoy a scenic drive northeast for approximately 4.5 hours; pack some snacks and entertainment for your 18-month-old son.
Fuel cost approx. USD40, 4h30m

12:30pm

Lunch at Flatbread Company Portsmouth

Order organic, wood-fired pizzas that the whole family will enjoy, including kid-friendly options in a cozy, rustic atmosphere.
USD30, 1h

1:30pm

Afternoon Nap Time

Check into your Portsmouth accommodation and enjoy some quiet time for the little one’s nap from 1 to 3 pm.
Included in hotel stay, 1h30m

3:00pm

Strawbery Banke Museum

Visit this interactive, living history museum with child-friendly exhibits and beautiful outdoor spaces for gentle walking and exploration.
Adults USD20, Children under 2 free, 2h

5:30pm

Visit Portsmouth Brewery

Relax at this local brewery known for family-friendly environment and good craft beers. They also offer non-alcoholic options and kids’ snacks.
USD15, 1h

7:00pm

Dinner at The Portsmouth Gas Light Co.

Enjoy a delicious meal with a mix of pizzas and New England cuisine in a comfortable setting suitable for families.
USD40, 1h30m
Find Hotels in Cold Spring

Day 2: Portsmouth to Kittery

Portsmouth, NH to Kittery, ME on September 25, 2025

8:00am

Breakfast at The Friendly Toast

Start your morning with a lively diner atmosphere and creative breakfast dishes with kid-friendly options.
USD25, 1h

9:30am

Bike ride on the Piscataqua Riverwalk

Enjoy a scenic, flat bike ride along the riverfront which is stroller- and kid-friendly, giving great views and fresh air.
Bike rental approx. USD15 per adult, 1h30m

11:00am

Visit Discover Portsmouth Visitor Center

Pick up maps and local guides for family-friendly attractions and learn little historical tidbits about Portsmouth.
Free, 0h30m

11:30am

Visit Seacoast Science Center

An excellent kid-friendly spot with interactive exhibits focused on marine life, perfect for toddlers to explore and learn through play.
USD12 adults, under 2 free, 1h30m

1:00pm

Nap Time at your Portsmouth accommodation

Return for your child’s nap, allowing some rest before afternoon travel.
Included in hotel stay, 2h

3:00pm

Drive to Kittery, Maine

A short 20-minute drive to nearby Kittery for an afternoon of light exploring and settling in.
Fuel cost negligible, 0h20m

3:30pm

Walk around Kittery Foreside

Stroll the quaint waterfront area with plenty of shops, a small playground, and ocean views that are perfect for relaxing.
Free, 1h

5:00pm

Visit Stoneface Brewing Co.

Enjoy the family-friendly atmosphere of this brewery with spacious outdoor areas and good local craft beers and snacks.
USD15, 1h

6:30pm

Dinner at Robert’s Maine Grill

A casual dining spot offering fresh seafood and pizza options in a family-friendly environment.
USD40, 1h30m
Find Hotels in Portsmouth

Day 3: Explore Kittery & Relax

Kittery, ME on September 26, 2025

8:00am

Breakfast at Kittery Trading Post Cafe

Enjoy a hearty breakfast with locally-sourced ingredients and kid-friendly dishes to start the day right.
USD20, 1h

9:30am

Visit Children's Museum of New Hampshire (Portsmouth)

Approximately 15 minutes drive back toward Portsmouth, this museum provides excellent interactive exhibits geared towards toddlers, ideal for stimulating play and learning.
USD12 adults, children under 2 free, 2h

11:30am

Return to Kittery for Lunch at Camber Kitchen & Bar

This restaurant offers creative yet approachable dishes including pizzas and kid-friendly meals, perfect for a relaxed lunch.
USD35, 1h

1:00pm

Nap Time at accommodation

Give your youngster a good afternoon rest with a quiet period at your lodging.
Included, 2h

3:00pm

Bike or walk the Rachel Carson National Wildlife Refuge trails

Enjoy easy walking or a gentle bike ride in nature with plenty of open space and scenic marsh views that are stroller friendly.
Free, 2h

5:30pm

Visit Buoy Brewing Co.

Family-friendly brewery with spacious outdoor seating and great drink options for parents while kids can enjoy some open space.
USD15, 1h

7:00pm

Dinner at Gritty McDuff’s Brew Pub Kittery

Relax with classic pizza and pub fare in a friendly environment that welcomes families with young children.
USD40, 1h30m
Find Hotels in Kittery

Day 4: Return to LGA

Kittery, ME to LaGuardia Airport, NY on September 27, 2025

7:30am

Breakfast at local bakery in Kittery

Grab fresh pastries, coffee, and quick bites to enjoy before starting your return journey.
USD15, 0h45m

8:30am

Drive back to LaGuardia Airport, NY

Set off on your approximately 5-hour drive south to New York City, taking breaks as needed for the toddler.
Fuel cost approx. USD45, 5h

1:30pm

Lunch stop at a family-friendly restaurant near New Haven, CT

Take a break and enjoy some classic pizza at a popular spot like BAR or Frank Pepe Pizzeria Napoletana, catering to families.
USD30, 1h

2:30pm

Continue drive to LaGuardia Airport

Complete your trip home with restful stops as needed to keep the little one comfortable.
Fuel costs included, 2h30m
Find Hotels in Kittery
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