Best Beginner-Friendly Winter Hikes with Toddlers in New England
Winter hiking with toddlers might sound intimidating, but New England offers incredible trails that are perfect for little adventurers! There's something magical about experiencing snow-covered forests, frozen waterfalls, and winter wonderlands with your kids. After camping and hiking throughout the White Mountains and Green Mountains (we absolutely loved our summer camping trip to the Greens!), I've gathered some of the best beginner-friendly winter trails across the region.
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Before we dive in, if you're new to winter hiking with little ones, make sure to check out my posts on how to dress babies and toddlers for winter hiking and hiking with babies in general to feel confident and prepared!
White Mountains, New Hampshire
The White Mountains are our go-to destination - we camp there regularly and love discovering new trails and campgrounds each visit. Something to keep in mind when in the White Mountains is parking; just because there are parking lots at trailheads does not mean you will find a parking spot. I recommend going early in the day to get a parking spot; otherwise, you may be walking a bit to some of the trailheads, especially in the fall during leaf-peeping season. Here are some winter-friendly options for families:
1. Artist's Bluff Trail (Franconia Notch)
Length: 1.5 miles round trip
Views: Absolutely stunning! Panoramic views of Franconia Notch, Echo Lake, and the surrounding peaks
Parking: Large parking area at the trailhead off I-93
Dogs: Allowed on-leash
Winter Activities: Snowshoeing is recommended when there's significant snow
Notes: This short hike packs a serious punch with its views. The trail is steep in sections but manageable with toddlers who can walk. Not stroller-friendly due to rocky terrain. The summit is perfect for snack time with those incredible vistas!
2. Greeley Ponds Trail (Kancamagus Highway)
Length: 4.4 miles round trip (but you can turn around earlier)
Views: Beautiful forest scenery and two pristine mountain ponds
Parking: Parking area on Kancamagus Highway
Dogs: Allowed on-leash
Winter Activities: Excellent for snowshoeing and cross-country skiing
Notes: The trail is relatively flat, making it perfect for toddlers. You don't have to go all the way to the ponds - even a short walk in gives you that peaceful winter forest experience. The wide trail makes it great for families.
3. Sabbaday Falls (Kancamagus Highway)
Length: 0.6 miles round trip
Views: Gorgeous frozen waterfall
Parking: Small parking area; arrive early in winter
Dogs: Allowed on-leash
Winter Activities: Snowshoeing when conditions require
Notes: This is one of the shortest hikes on the list! The frozen falls are spectacular and toddler legs can definitely handle this distance. The trail has some stairs and wooden bridges, so not stroller-friendly but manageable for young hikers.
4. Lower Falls (Albany, NH)
Length: 0.8 miles round trip
Views: Beautiful cascading falls that freeze into ice sculptures
Parking: Small roadside parking area
Dogs: Allowed on-leash
Winter Activities: Great for snowshoeing
Notes: Short and sweet! This trail follows along the Swift River and is relatively flat. Perfect for toddlers, and the frozen falls are mesmerizing. The trail can be icy, so microspikes can be helpful.
Green Mountains, Vermont
We fell in love with the Green Mountains during our summer camping trip, and they're equally magical in winter! The terrain tends to be a bit gentler than the Whites, making them perfect for families.
5. Stowe Pinnacle Trail
Length: 2.8 miles round trip
Views: 360-degree views from the summit on clear days
Parking: Small parking area - it can fill up on the weekends
Dogs: Allowed on-leash
Winter Activities: Snowshoeing recommended
Notes: While this hike has some elevation gain, it's steady and manageable. The views are worth it! Not stroller-friendly, but toddlers who enjoy hiking will feel accomplished at the top.
6. Texas Falls Nature Trail (Hancock, VT)
Length: 1.2 miles round trip
Views: Stunning frozen waterfalls and gorge
Parking: Designated parking area at the recreation area
Dogs: Allowed on-leash
Winter Activities: Snowshoeing when snowy
Notes: This trail is relatively flat with interpretive signs along the way. The frozen falls create incredible ice formations. The wide, well-maintained trail makes it accessible for families. Partially stroller-friendly in light snow conditions.
7. Owl's Head Trail (Groton State Forest)
Length: 2.5 miles round trip
Views: Fire tower at the summit with panoramic views
Parking: Parking area at trailhead
Dogs: Allowed on-leash
Winter Activities: Excellent for snowshoeing
Notes: The fire tower is a huge hit with kids! The climb is steady but not too steep. Plan for extra time at the top so your toddler can enjoy the tower experience.
Massachusetts Mountains
8. Mount Wachusett (Princeton, MA)
Length: Multiple trail options; Balance Rock Trail is 2.2 miles round trip
Views: Incredible 360-degree views from the summit - you can see Boston on clear days!
Parking: Large parking area at Wachusett Mountain State Reservation visitors center and several parking areas at various trailheads around the mountain
Dogs: Allowed on-leash
Winter Activities: Cross-country skiing and snowshoeing; the summit road is sometimes open for driving
Notes: As Massachusetts' highest peak east of the Connecticut River, Wachusett offers amazing views! The Balance Rock Trail is the most family-friendly option with steady but manageable elevation. When the summit road is open in winter, you can drive most of the way up. The visitors center has restrooms - a huge plus with toddlers!
9. Mount Watatic (Ashburnham, MA)
Length: Wapack Trail approach is 2 miles round trip
Views: Beautiful views of Mount Monadnock and the surrounding area
Parking: Parking area on Route 119
Dogs: Allowed on-leash
Winter Activities: Snowshoeing is highly recommended
Notes: This is a hidden gem! The trail is rocky in sections but short enough for determined toddlers. The open summit is perfect for running around and taking in the views. It's less crowded than other popular peaks, giving you a more peaceful experience. Not stroller-friendly due to rocky terrain.
10. Mount Sugarloaf (South Deerfield, MA)
Length: Summit Road allows driving or 1.5 miles hiking
Views: Spectacular Connecticut River Valley views
Parking: Large parking area at the summit (when road is open) or base
Dogs: Allowed on-leash
Winter Activities: Snowshoeing on trails
Notes: You can often drive to the summit when conditions are good, making this incredibly toddler-friendly! If hiking, the trail is moderate. The observation tower at the top is perfect for little ones. Some trails are wide enough for strollers in packed snow.
11. Monument Mountain (Great Barrington, MA)
Length: 2.5-3 miles (various loop options)
Views: Beautiful Berkshire hills vistas
Parking: Parking lot at the trailhead on Route 7
Dogs: Allowed on-leash
Winter Activities: Snowshoeing is popular here
Notes: While there are steeper sections, you can tailor the hike to your toddler's ability. The Hickey Trail is the gentler option. The summit rocks are fun for kids to explore. Not stroller-friendly due to rocky terrain.
Connecticut
12. Sleeping Giant State Park (Hamden, CT)
Length: Tower Trail is 3.2 miles round trip, but shorter options are available
Views: Stone observation tower with views of Long Island Sound
Parking: Large parking lot at the main entrance
Dogs: Allowed on-leash
Winter Activities: Cross-country skiing and snowshoeing are allowed on designated trails
Notes: This park has multiple trail options! The Tower Trail is the most popular, but you can choose shorter routes. The tower is a big attraction for kids. Some of the wider paths are stroller-friendly in winter with appropriate stroller equipment.
13. Talcott Mountain State Park (Simsbury, CT)
Length: 2.5 miles round trip
Views: Heublein Tower offers incredible valley views
Parking: Parking area at the trailhead
Dogs: Allowed on-leash
Winter Activities: Great for snowshoeing
Notes: The wide, well-maintained trail is perfect for families. The historic Heublein Tower at the summit is fascinating for kids. Generally less crowded in winter, giving you peaceful family time on the trail.
14. Wadsworth Falls State Park (Middletown, CT)
Length: Multiple trail options; Main Falls Trail is 1 mile round trip
Views: Beautiful waterfalls that create stunning ice formations in winter
Parking: Large parking area at the park entrance
Dogs: Allowed on-leash
Winter Activities: Snowshoeing on trails
Notes: The short hike to the main falls is perfect for toddlers! The 30-foot waterfall is gorgeous when partially frozen. The park has easier, wider trails that work well for families. You can explore additional trails if your toddler wants more adventure. Some sections are flat enough for all-terrain strollers in light snow.
Rhode Island
15. Stepstone Falls Trail (West Greenwich, RI)
Length: 2.5 miles loop
Views: Series of cascading falls along Falls River
Parking: Small parking area on Escoheag Hill Road
Dogs: Allowed on-leash
Winter Activities: Snowshoeing when conditions permit
Notes: This relatively flat trail follows along the river with multiple waterfall viewpoints. The falls are beautiful when partially frozen. The loop is manageable for toddlers, or you can do an out-and-back for a shorter option. Not stroller-friendly but very toddler-walkable.
16. Vin Gormley Trail at Ninigret Park (Charlestown, RI)
Length: 1.8 miles loop
Views: Scenic views of Ninigret Pond and the surrounding conservation area
Parking: Large parking area at Ninigret Park
Dogs: Allowed on-leash
Winter Activities: Snowshoeing; flat terrain makes it accessible in winter
Notes: This easy, mostly flat trail loops through woodlands and offers peaceful winter scenery. The wide, well-maintained path makes it perfect for families with toddlers. Partially stroller-friendly with all-terrain strollers in light snow conditions. Great for a quick winter walk when you want something low-key!
17. Walkabout Trail at Arcadia Management Area (Exeter, RI)
Length: 8 miles loop (but easily do shorter sections)
Views: Diverse forest scenery, peaceful woodland atmosphere
Parking: Multiple access points; parking at Arcadia Road
Dogs: Allowed on-leash
Winter Activities: Excellent for snowshoeing
Notes: Don't let the total distance intimidate you! The Walkabout Trail is well-marked and you can turn around at any point. Even a short out-and-back gives you a beautiful winter forest experience. The trail is relatively flat with gentle terrain perfect for toddlers who love exploring. This is Rhode Island's largest management area, so you'll enjoy peaceful, uncrowded trails.
Maine
18. Sabattus Mountain (Lovell, ME)
Length: 1.8 miles round trip
Views: Gorgeous views of the White Mountains and surrounding lakes
Parking: Small parking area at the trailhead
Dogs: Allowed on-leash
Winter Activities: Snowshoeing recommended
Notes: Short but with some elevation gain. The trail is well-marked and the summit views are spectacular - especially seeing the White Mountains from a distance! This is a great confidence-builder for toddler hikers.
19. Jordan Pond Path (Acadia National Park)
Length: 3.3 miles loop (can turn around early for shorter hike)
Views: Stunning views of Jordan Pond with the Bubbles mountains as a backdrop
Parking: Parking at Jordan Pond House (arrive early - this is a very popular area in Acadia!)
Dogs: Allowed on-leash
Winter Activities: Snowshoeing; portions on boardwalks
Notes: This is one of Acadia's most iconic and family-friendly trails! The relatively flat loop circles Jordan Pond with beautiful scenery the entire way. Parts of the trail feature rustic boardwalks. You can do just a portion and turn back, or start at Jordan Pond House and walk counterclockwise for a quarter mile to see the stone bridges - perfect for toddlers! The wide trail works well with winter conditions.
20. Acadia Carriage Roads (Multiple Locations in Acadia National Park)
Length: Variable - choose your own distance!
Views: Beautiful forest scenery, mountain views, and frozen ponds
Parking: Multiple access points: Eagle Lake parking lot, Hulls Cove Visitor Center, Brown Mountain Gatehouse
Dogs: Allowed on-leash (stay on designated side of groomed trail)
Winter Activities: Cross-country skiing is excellent here! The carriage roads' crushed-stone surfaces are ideal for Nordic skiing, and volunteers from the Acadia Winter Trails Association groom over 25 miles of trails for both classic and skate skiing when conditions permit. Snowshoeing is also popular.
Notes: Acadia's 45 miles of historic carriage roads offer gentle slopes perfect for families! Popular routes include the Witch Hole Loop (6.5 miles) and Aunt Betty Loop (6 miles), but you can turn around at any point. The wide, relatively flat paths are extremely toddler-friendly - you can even bring a jogging stroller with appropriate winter tires or a stroller ski attachment! When groomed for skiing, follow trail etiquette: one side is for skiers, the other for snowshoers and walkers. This is a magical winter experience with stunning scenery and much fewer crowds than in the summer!
21. Ship Harbor Trail (Acadia National Park)
Length: 1.3 miles figure-8 loop
Views: Beautiful coastal views and bird habitats
Parking: Parking area at the trailhead near Seawall
Dogs: Allowed on-leash
Winter Activities: Snowshoeing when snowy
Notes: This easy, relatively flat trail along the coast is perfect for families! The figure-8 design means you can do just one loop if toddlers are tiring. Great for exploring the shoreline and looking for winter birds. It is less crowded than other Acadia trails, giving you a peaceful family experience.
Gear Up for Your Winter Adventures!
Looking for the right gear to make your winter hikes comfortable and safe? Check out my Amazon Hiking + Camping List for all my tried-and-true recommendations! From toddler carriers and microspikes to thermoses and layering essentials, I've curated everything we actually use and love on our family adventures.
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Winter Hiking Tips for Success
Timing is Everything: Start early to ensure you're off the trail before it gets dark and cold. Winter days are short!
Bring Extra Everything: Extra mittens, extra snacks, extra layers. Toddlers are unpredictable, and winter conditions demand backup supplies.
Make it Fun: Let your toddler set some of the pace, take breaks to explore snow, make snowballs, or look for animal tracks. It's about the experience, not the speed!
Check Conditions: Trail conditions can vary dramatically in winter. Check recent trip reports and weather forecasts before heading out.
Consider Microspikes: Even on beginner trails, winter conditions can make footing tricky. Microspikes or other traction devices are essential for adult hikers.
Pack the Essentials: Warm drinks in a thermos, high-energy snacks, first aid kit, and extra lighting are all winter necessities.
Final Thoughts
Winter hiking with toddlers opens up a whole new world of outdoor adventure! The White Mountains and Green Mountains have become our family's favorite destinations - there's always a new campground to discover or trail to explore. These beginner-friendly hikes offer the perfect introduction to winter wilderness while keeping things manageable for little legs.
Remember, the goal isn't reaching the summit or completing the full trail - it's creating magical winter memories with your little ones. Turn back when you need to, celebrate small victories, and enjoy the peaceful beauty of New England's winter wonderland together.
Happy trails, Untamed Mamas!