New England

12 Best New England Family-Friendly Hikes

Pack up the kiddos and take in nature’s beauty with this collection of vista-filled New England family-friendly hikes.

By Ian Aldrich

Sep 12 2022


Mount Monadnock | New Hampshire Hiking

Photo Credit : Cathryn McCann
From a seaside adventure on Block Island to a New Hampshire mountain that’s one of the most climbed in the world, New England has thousands of miles of trails that cater to families with kids of almost any age. Big peaks, big views, and big fun are all part of the experience. Ready to hit the trail? Then fill up the water bottles, grab some energy bars, and read on for our selection of the best New England family-friendly hikes.
12 Best New England Family-Friendly Hikes
The White Cross Trail is a popular route on New Hampshire’s Mount Monadnock, one of our picks for the best New England family-friendly hikes.
Photo Credit : Cathryn McCann

12 Best New England Family-Friendly Hikes

Maine Family Hikes

Ship Harbor Trail | Acadia National Park

Pick up a trail guide at the park visitors’ center and bring a picnic. This gentle 1.3-mile figure-eight hike passes through varied ecosystems, from moss-laden woods to pink granite ledges, and provides wonderful views of Acadia’s rocky coast.

Rattlesnake Mountain | Raymond

Don’t be deterred by the ominous reptilian name: Rattlesnake Mountain via the Bri-Mar Trail is a moderate 2.5-mile out-and-back hike that — while steep in some places — is dog-friendly and kid-appropriate. Look for a great shot of Panther Pond just half a mile in.

New Hampshire Family Hikes

Mount Monadnock | Jaffrey

It’s a National Natural Landmark and one of the most-climbed mountains in the world for a reason. Though you can take your pick from any of its beautiful trails, we recommend that first-time Monadnock hikers — or even first-time hikers, which is often the case at this mountain — head up to the top via the White Dot Trail and descend by way of the White Cross Trail (about 4.2 miles up and back). At the bald summit, surrounded by thousands of acres of protected highlands, you can look out toward Boston, nearly 100 miles away.

Mount Willard Trail | Hart’s Location

If the thought of mountain climbing makes you sweat long before leaving your car, wipe your brow and give Mount Willard a try. In less than an hour after setting out on this 2.8-mile round-trip hike, you’ll make it to the peak, where stunning views of Crawford Notch stand before you.  

Vermont Family Hikes

Snake Mountain | Addison & Weybridge

Vermont’s Green Mountains may be the star attraction, but when you’re short on time and energy, you can’t beat Snake, a 1,287-foot outlier of the Taconic range that rises abruptly from the surrounding terrain to offer the state’s finest panorama of dairy lands, Lake Champlain, and the Adirondacks. Park in the lot on Mountain Road and walk less than a quarter mile to the well-marked trailhead on the left. Follow the Old Carriage Road 1.5 miles to the top, where you’ll find a cement platform from the 1870 Grand View Hotel that once stood here; now it’s a great spot for picnics. Named a 2018 Yankee Editors’ Pick for “Best Short Hike.”

Sterling Pond Trail | Jeffersonville

This moderate trail in Smugglers’ Notch State Park is about 2.8 miles out and back, and while steep and rocky in some portions, the path is well maintained and leads to gorgeous views — and Vermont’s highest-elevation trout pond, to boot. Sterling Pond has been described as “idyllic” and is a great escape during the quieter fall months.

Massachusetts Family Hikes

Middlesex Fells Reservation | Stoneham

With 2,575 acres spanning five towns, a range of terrain, and a no-excuses travel distance from Boston, Middlesex Fells Reservation is an ideal destination for outdoor activities of all kinds. There are a number of beautiful natural features at the Fells, including Sheepfold Meadow, a 10-acre open field, and Wright’s Tower, which looks out over the Boston Basin, plus ponds and plenty of wooded areas. Budding naturalists will love the easy, mile-long Long Pond Nature Trail, which has a nature pamphlet describing plants, animals, and geology along the way.

Skyline Loop | Milton

Great Blue Hill (635 feet), just south of Boston, is the highest peak in the Blue Hills Reservation and also the highest summit south of Maine that’s near the Atlantic Ocean. In just three miles round-trip, hikers can hit several summits in the Blue Hills range, including Great Blue Hill, and visit Eliot Tower and the Blue Hill Observatory. Additionally, the reservation has 125 miles of trails with a range of easy to rugged terrain, so there are plentiful opportunities to add on to or switch up your hike. 

Stony Ledge | Williamstown

You can sidestep the exertion of summiting Mount Greylock, Massachusetts’s highest peak, while still reaping its visual rewards when you stride up the 1.9-mile-long unpaved Sperry Road to the Stony Ledge outlook. It offers a vertiginous 1,400-foot view into the Hopper, a steep-sided bowl notable for old-growth woods, with a majestic panorama of the Bay State’s highest peaks.

Rhode Island Family Hikes

Clay Head Trail | Block Island

First, this 3.5-mile out-and-back trail in Clay Head Preserve descends into a marshy area; then it climbs into a sunny meadow, all the while providing a low, rumbling thunder-like soundtrack from the crashing surf below. And then suddenly you’re there: at the edge of a high, sandy bluff, gazing across sparkling water to what in Block Island–speak is called “America,” or mainland Rhode Island. 

Rome Point Trail | Saunderstown

This 2.4-mile loop in the John H. Chafee Nature Preserve is perfect for hikers and walkers of all skill levels (and their leashed pups). The trail starts inland and leads out to the bay, and the constant scenery change makes for an exciting quick trip. As a result, this trail — also known as the “seal hike” for its view of seals in the bay — is very popular during the summer, so to beat the crowds, make plans to go in the fall. 

Connecticut Family Hikes

Talcott Mountain Yellow Trail | Simsbury

While Talcott Mountain State Park has other routes to the top, the 2.5-mile Yellow Trail loop is a popular and family-friendly way to reach the summit and its 165-foot Heublein Tower. Prepare to pause often to admire the ever-expanding views of the verdant Farmington Valley; to the southeast, Hartford’s skyline juts up from the landscape, looking regal and remote. Named a 2018 Yankee Editors’ Pick for “Best Short Hike.” Which New England family-friendly hikes would you add to the list? Let us know in the comments below!

See More:

Best New England Hikes for Kids at Every Age

10 Best White Mountain Day Hikes