Our favorite short hikes in the South Berkshires
Your perfect before-lunch walk in the woods
I’ve loved being in the woods since I was a little kid. I grew up near a hundred-acre patch of woods with creeks, rocky outcroppings, and beautiful meadows, and every day I couldn’t wait to stroll through the beauty and tranquility of the forest.
Now that I run a bed and breakfast in the Berkshires, I don’t have a lot of time for long hikes. Fortunately, we have amazing short hikes within minutes of the Wilder House in Sheffield. Here are a few of my favorites.
1. Race Brook Trail to Upper Race Falls (7 minutes from Wilder House)
This ascending hike takes you from Undermountain Rd (Rt 41) in Sheffield uphill to Race Falls, an impressive 3-tiered waterfall that really roars in the spring and early summer. The trail offers an eastward view over the South Berkshires (though it’s best to view when the foliage is thin). It’s just about 3 miles roundtrip from the parking lot to the falls and back. But if you’re really feeling adventurous, you can continue uphill to the Appalachian trail, and extend the hike for miles in the Taconic Range on Mount Washington.
2. Jug End State Preservation (15 minutes from Wilder House)
Until the 1980s, Jug End was a popular destination for skiing with miles of cross-country trails and a 4-season hotel and resort. Today, it’s nature preserve with a three-mile loop trail that includes forest, stream, and meadow. While the Berkshires are known for being quiet, Jug End is in an especially sparse part of Berkshire County, making this an awesome place to be alone with your thoughts while you hike.
3. Bartholomews Cobble Reservation (8 minutes from Wilder House)
Bartholomews Cobble is part of the Trustees of Reservations system, meaning it’s been preserved for its historical significance and natural beauty. This gentle trail system offers sweeping views of the Taconic Ridge and incredible birding in a unique meadow ecosystem.
4. Goodnow Preserve (16 minutes from Wilder House)
Goodnow preserve is a beautiful park in the community of Mill River, with a 2.5 mile loop trail partially along the clear waters of the Konkapot River. With rolling hills, historic stone walls and the ruins of an old Mill, Goodnow is a true gem to our east. While you’re here, swing by the
Southfield Store for lunch or pick up some locally curated snacks from the
Mill River General Store.
5. Roger and Virginia Drury Preserve (4 minutes from Wilder House)
The Roger and Virginia Drury Preserve in Sheffield offers a 2.5-mile round-trip hike through a lowland forest rich in wildlife. The Drury Trail leads to Schenob Brook, providing views of Mount Race and opportunities for birdwatching, with sightings of herons and kingfishers. The preserve is home to coyotes, bobcats, and turkeys, and snowshoeing in winter allows visitors to track animal footprints across the virgin snow.
Do you have a favorite local hike? Please tell us about it when you visit Wilder House, our highly-rated bed and breakfast in the Berkshires. We hope to see you soon!
- Brad
