Family Road Trip from Cold Spring to Portsmouth, Kittery & Providence with Toddler-Friendly Activities

Day 1: Travel & Portsmouth Fun

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

7:00am

Breakfast at Cold Spring Pizza

Start your journey with delicious breakfast pizza or pastries from this cozy local spot to fuel the day ahead.
USD15, 0h45m

8:00am

Drive to Portsmouth, NH

Enjoy a scenic 4.5-hour drive north with family-friendly stops for snacks and toddler entertainment.
Fuel approx. USD40, 4h30m

12:30pm

Lunch at Flatbread Company Portsmouth

Delight in organic wood-fired pizzas with great kid-friendly options in a lively atmosphere.
USD30, 1h

1:30pm

Nap Time at accommodation

Rest time for your toddler back at your lodging to recharge for the afternoon.
Included, 1h30m

3:00pm

Visit Strawbery Banke Museum

Explore this outdoor living history museum with easy walking paths and interactive exhibits perfect for young children.
USD20 adults, children under 2 free, 2h

5:30pm

Portsmouth Brewery

Enjoy local craft beers in a family-friendly brewery with snacks and a welcoming environment for kids.
USD15, 1h

7:00pm

Dinner at The Portsmouth Gas Light Co.

Dine on delicious pizzas and New England fare in a casual, family-appropriate setting.
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

Start the day with creative, hearty breakfast selections served in a bright, kid-friendly atmosphere.
USD25, 1h

9:30am

Bike ride along Piscataqua Riverwalk

Enjoy a picturesque and stroller-friendly bike path with lovely river views, great for all ages.
Bike rental around USD15 per adult, 1h30m

11:00am

Portsmouth Visitor Center

Pick up guides and get recommendations for family-friendly activities and historical sites nearby.
Free, 0h30m

11:30am

Seacoast Science Center

Explore marine exhibitions and tidepools designed to engage toddlers and nurture curiosity outdoors.
USD12 adults, under 2 free, 1h30m

1:00pm

Nap Time at accommodation

Return to your lodging to relax and nap after a morning of exploring.
Included, 2h

3:00pm

Drive to Kittery, ME

A short scenic drive to Kittery to enjoy the coastal charm and settle in for the evening.
Fuel minimal, 0h20m

3:30pm

Walk around Kittery Foreside

Leisurely stroll the waterfront area, visit quaint shops, and enjoy a playground suited for toddlers.
Free, 1h

5:00pm

Stoneface Brewing Company

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

6:30pm

Dinner at Robert’s Maine Grill

Savor fresh seafood and pizza in a warm, family-friendly environment to end your day.
USD40, 1h30m
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Day 3: Kittery Exploration and Providence Drive

Kittery, ME to Providence, RI on September 26, 2025

8:00am

Breakfast at Kittery Trading Post Cafe

Enjoy a locally loved breakfast spot with fresh ingredients and toddler-friendly dishes.
USD20, 1h

9:30am

Visit Children’s Museum of New Hampshire

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

11:30am

Lunch at Camber Kitchen & Bar, Portsmouth

Casual lunch spot serving pizzas and family-friendly meals in a relaxed atmosphere.
USD35, 1h

1:00pm

Nap Time at lodging

Take a restful break at your accommodation to prepare for afternoon travel.
Included, 2h

3:00pm

Drive to Providence, RI

Enjoy a scenic 1.5-hour drive south to Providence and settle into your accommodation.
Fuel approx. USD20, 1h30m

4:30pm

Stroll along Waterplace Park

Take a gentle walk on waterfront paths that are stroller friendly and perfect for winding down the day.
Free, 1h

6:00pm

Dinner at Al Forno

Famous for wood-fired pizza and Italian dishes, offering a cozy, family-friendly dining experience.
USD45, 1h30m
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Day 4: Providence Departure

Providence, RI on September 27, 2025

8:00am

Breakfast at Seven Stars Bakery

Enjoy fresh pastries and breakfast fare in a warm, inviting bakery perfect for families.
USD20, 0h45m

9:00am

Explore Roger Williams Park Zoo

Visit the family-friendly zoo with exhibits and play areas designed for toddlers and kids of all ages.
USD20 adults, under 2 free, 2h

11:15am

Lunch at Wildflour Vegan Bakery & Juice Bar

Casual lunch spot with healthy, fresh food options including toddler-friendly items.
USD25, 1h

12:30pm

Nap or quiet time at hotel

Relax before your afternoon departure to help your toddler rest before the flight.
Included, 2h

2:30pm

Prepare for flight and head to Providence Airport

Allow plenty of time for car return, security, and toddler comforts before your 5:00 pm flight.
Taxi or rideshare approx. USD30, 1h
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