Family-Friendly New England Road Trip: Cold Spring to Portsmouth, Kittery & Boston with Toddler Fun

Day 1: Travel & Portsmouth Fun

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

7:00am

Breakfast at Cold Spring Pizza

Begin your day with a warm breakfast pizza or pastries from this local gem to start the journey energized.
USD15, 0h45m

8:00am

Drive to Portsmouth, NH

Embark on a scenic 4.5-hour drive northeast with ample snacks and entertainment for your toddler.
Fuel approx. USD40, 4h30m

12:30pm

Lunch at Flatbread Company Portsmouth

Savor organic, wood-fired pizzas with kid-friendly options in a fun and relaxed setting.
USD30, 1h

1:30pm

Nap Time at accommodation

Rest and recharge at your hotel while your little one enjoys nap time.
Included, 1h30m

3:00pm

Strawbery Banke Museum

Explore this living history museum with engaging outdoor spaces and toddler-friendly activities.
USD20 adults, under 2 free, 2h

5:30pm

Portsmouth Brewery Visit

Relax in a family-friendly brewery with great craft beers and kid snacks.
USD15, 1h

7:00pm

Dinner at The Portsmouth Gas Light Co.

Enjoy a cozy atmosphere offering pizzas and New England dishes suitable for families.
USD40, 1h30m
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Day 2: Portsmouth to Kittery

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

8:00am

Breakfast at The Friendly Toast

Creative and hearty breakfast selections in a vibrant, family-friendly atmosphere.
USD25, 1h

9:30am

Bike ride on Piscataqua Riverwalk

Enjoy a scenic and stroller-friendly bike path with river views suitable for all ages.
Bike rental approx. USD15 per adult, 1h30m

11:00am

Discover Portsmouth Visitor Center

Gather insights and maps for family-friendly stops and historical highlights nearby.
Free, 0h30m

11:30am

Seacoast Science Center

Engaging marine life exhibits perfect for toddlers to explore and discover hands-on activities.
USD12 adults, under 2 free, 1h30m

1:00pm

Nap Time at accommodation

Return to relax and refresh before afternoon travel.
Included, 2h

3:00pm

Drive to Kittery, ME

Short scenic drive to Kittery to settle in and enjoy the coastal charm.
Fuel negligible, 0h20m

3:30pm

Walk around Kittery Foreside

Leisurely stroll the waterfront, quaint shops, and visit a local playground for your toddler.
Free, 1h

5:00pm

Stoneface Brewing Co.

Relax in a spacious, family-friendly brewery with outdoor seating and good local craft beers.
USD15, 1h

6:30pm

Dinner at Robert’s Maine Grill

Fresh seafood and tasty pizza options in a welcoming, family-appropriate environment.
USD40, 1h30m
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Day 3: Kittery Exploration & Boston Arrival

Kittery, ME to Boston, MA on September 26, 2025

8:00am

Breakfast at Kittery Trading Post Cafe

Enjoy a local-favorite breakfast with fresh ingredients and toddler-friendly options.
USD20, 1h

9:30am

Children's Museum of NH (Portsmouth)

Drive about 15 minutes to Portsmouth to visit this interactive museum with exhibits designed for toddlers.
USD12 adults, under 2 free, 2h

11:30am

Lunch at Camber Kitchen & Bar, Portsmouth

Casual and tasty lunch featuring pizzas and family-friendly dishes for all tastes.
USD35, 1h

1:00pm

Nap Time at lodging

Rest time to recharge before heading to Boston.
Included, 2h

3:00pm

Drive to Boston, MA

Begin the 1.5 to 2-hour drive south to Boston, settling in for your final night.
Fuel approx. USD15, 2h

5:00pm

Stroll Boston Common & Public Garden

Enjoy a leisurely walk in Boston’s iconic parks, with stroller-friendly paths and a playground for toddlers.
Free, 1h

6:15pm

Dinner nearby Boston Common – Fajitas & ’Ritas

Family-friendly dining with a casual atmosphere offering pizza and other kid-pleasing dishes close to your hotel.
USD40, 1h
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Day 4: Boston & Flight Home

Boston, MA on September 27, 2025

7:30am

Breakfast at Tatte Bakery & Cafe

Delight in delicious pastries and breakfast fare in a cozy spot loved by locals and families.
USD20, 0h45m

8:30am

Visit Boston Children’s Museum

Take advantage of reciprocal benefits at this museum full of interactive exhibits perfect for your toddler.
Reciprocal membership discounts, 2h

10:30am

Explore the New England Aquarium

Visit family-friendly exhibits featuring marine life, perfect for sensory engagement and learning.
USD30 adults, under 2 free, 2h

12:30pm

Lunch at Regina Pizzeria

Enjoy iconic Boston-style pizza in a kid-friendly setting, great for a final meal in the city.
USD35, 1h

1:30pm

Nap or quiet rest at hotel

Give your toddler rest before preparing for departure.
Included, 2h

3:30pm

Visit Boston Public Library Courtyard

Relax in this beautiful open space with quiet areas and sometimes kid activities available on weekends.
Free, 1h

4:30pm

Head to Boston Logan Airport

Leave early to allow ample time for car rental return, security, and toddler comfort before your 6:45 pm flight.
Taxi or rideshare approx. USD40, 1h15m
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