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Blog :: 05-2015

5 Top Spots for Hiking with Kids in Southern Vermont

Whether it's spring, summer, or fall, hiking with kids in southern Vermont is a great way to spend some family time outdoors. On top of fresh air and exercise, a good hike in Vermont gives kids the chance to connect with nature and learn about their surroundings. These five spots for hiking with kids have varying degrees of difficulty but are all on the medium-to-easy end of the spectrum. They're also easy to access. 

Mountain View - Hiking with Kids

Emerald Lake State Park

Located between the towns of Manchester and Rutland, Emerald Lake State Park has a wide network of hiking trails and footpaths encircling the 20-acre lake and surrounding woods. Some of the more wooded trails offer a good challenge for older children and adults, while young kids might prefer the easy trails such as the Lake Trail or Lower Trail. When you’re done hiking you can also enjoy a swim in the lake or a cookout in one of the park’s campsites before heading out.

Shaftsbury State Park

Another wonderful lakeside trail system, Shaftsbury State Park offers an excellent look at some southern Vermont wetlands and the animals and plants that inhabit them. The “Healing Springs Nature Trail” as it’s called lets visitors explore the area around Lake Shaftsbury and view native wildlife and vegetation up close all year round, and its short length and easy access means it a perfect place to go with children.

southern Vermont hiking trail Molly Stark State Park

Right outside of Wilmington you’ll find the Molly Stark State Park trail system. This easy-to-moderate area of hiking trails offers some good family-friendly hiking for older kids and adults, and it also connects to several other trail systems including the trails for the town of Wilmington and those located within the Hogback Mountain Conservation Area. Make sure you take a trail map with you or follow the blazes, since the trails have several branches that can lead you over quite a wide area.

Mount Snow Hiking Trails

With more than 20 miles of trails to explore, Mount Snow is a great place to visit during the warmer months of the year for some old-fashioned hiking fun. While not every trail is great for children - expect some challenges on some of the slopes - there are plenty of family-friendly areas for you to explore both on the mountain and in the nearby Deerfield Valley trails. Plus you can easily access all of Mount Snow’s amenities including restaurants and bathrooms, and you can also take advantage of other activities such as mountain biking, golf, and special events. One important tip: for safety reasons, hikers need to stay off the designated downhill mountain bike trails. 

Haystack Mountain Hiking Trail

This one is just up the road from us on route 100, and it's something of a rite of passage here at Chimney Hill. The Haystack Mountain hiking trail gives an awesome view of the Deerfield Valley, and at just over 1,000 vertical feet, it's manageable for most families. 

Hiking excursions big or small fare better with comfortable base camp nearby. If you're looking for a place to fill water bottles, mix granola, and unwind after your descent, a southern Vermont rental home is an excellent fit. 

Vermont Day Trips: Things to Do in Brattleboro, Vermont

With awesome hiking, skiing, biking, and more right here around Wilmington, plenty of visitors to the Hill are content to stay put once they arrive, and we can't blame them. Still, there's even more to be discovered on a short adventure downhill on Rt. 9. Within about a half hour's drive, you'll find a classic Vermont town with microbreweries, a vintage movie theater, a bursting arts scene, and plenty of family activities. These are just a few of our favorite things to do in Brattleboro, Vermont.  

Brattleboro, Vermont


Robb Family Farm

Even if you don’t have kids to take with you, the Robb Family Farm is a great way to experience some of Vermont’s most iconic traditions. The Robb Family Farm is a great way to see the process of making maple syrup and maple candies, and they also sell a variety of grass-fed, hormone-free meats to take home and enjoy.

Brattleboro Farmer’s Market

Each Saturday from spring until fall, vendors and shoppers take to the streets of Brattleboro for the weekly Farmer’s Market. More than 50 vendors selling produce, crafts, and food come together along with musicians and other entertainers to make this weekly event more of a celebration than a shopping trip. Come alone or bring the entire family – either way you’re sure to have a good time.

Shopping on Main Street

Looking for something for that special someone? Want to experience some authentic Vermont funkiness firsthand? Brattleboro’s Main Street shopping district won’t disappoint. Check out Beadnik’s for a unique and sometimes odd selection of gifts and curiosities, or take the kids to the Crafty Cauldron to make something firsthand. On your way home, swing by Twice Upon a Time to check out their huge selection of antiques and rarities from across Vermont and around the world.

Brattleboro Museum and Art Center Brattleboro Museum & Art Center

If you want to experience the culture and history of Vermont for yourself, look no further than the Brattleboro Museum and Art Center.  This museum, built from the shell of a former train station, showcases contemporary art with exhibits in all media, indoors and out. The museum also hosts frequent artist talks, concerts, and other cultural experiences, with either free or very modest admission prices. 

Brattleboro Retreat Trails

Feeling a little claustrophobic? Get out in the open on the Brattleboro Retreat Trails, a nine-mile network of hiking and multi-use trails that run right through town. These beautiful trails are well-maintained and easy to access, and they provide plenty of chances to get out and experience Vermont’s natural beauty. One of our favorites, the Tower Road, offers an awesome view of Brattleboro and the Connecticut River after only 15-20 minutes of hiking. 

Restaurants and Dining

In addition to the multitude of shopping and entertainment options in Brattleboro, there are also plenty of places to eat that will leave you feeling full without leaving your wallet empty. For casual food, great river views, and legendary house-made beers, check out Whetstone Station. Turquoise Grill has a top-notch burger along with Mediterranean and Turkish specialties. For date night, the two highest-end restaurants are Peter Havens and T.J. Buckley's

Brattleboro makes an easy day or evening trip, and it's right on your way if you're traveling to Chimney Hill via I-91. We highly recommend stopping in for dinner and a drink and leaving some time to wander around downtown. At one of our rental homes in Wilmington, VT, you'll have access to the perfect mix of mountain adventure and Vermont arts culture. 


  1. Tyan on

    Ha, I guess you've got a point, it's not zero impact like snow sheoing. But these trails are only for snowmobiles, in the off season they're closed. There's no destruction going on if you stay on the trail.
    • P.O. BOX 415, 9 Haystack Road, Wilmington VT 05363