Our favorite short hikes in the South Berkshires

Brad Sanzenbacher • September 12, 2024

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.


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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.


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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.


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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.


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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!


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- Brad


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Get ready, foodies! One of the absolute best reasons to visit the stunning Berkshires is our utterly incredible food scene. World-class chefs have set up shop here, creating dining experiences that truly surprise and delight. With so many fantastic restaurants around, it can be tough to choose, especially if you're just here for a quick weekend getaway. But don't you worry, we've got you covered! Here are some of our absolute favorite spots that you simply can't miss in the southern Berkshires. No Comply Foods - Great Barrington (Just 10 minutes from Wilder House) Prepare your taste buds for a treat at No Comply ! This casual spot in Great Barrington might feel laid-back with it's punk rock and vintage skateboard art, but its food packs a seriously big punch. Chef Steve Browning's menu is always a delightful surprise, constantly changing and always amazing. With unique flavors from around the world, No Comply is our go-to for dishes that expand your palate and leave you wanting more! Blackberry River Bistro - Canaan, CT (A quick 7 minutes from Wilder House) Tucked away on a corner in Canaan, Connecticut, you'll find the charming Blackberry River Bistro . This tiny gem, with just seven or eight tables, is run entirely by the amazing husband-and-wife team of Audrey and Sam Leary. While it's small, this bistro truly punches above its weight in food quality. We especially adore Audrey's incredible desserts and their always-changing pasta of the week! Roberto’s Pizza - Sheffield (Walking Distance from Wilder House) Ah, pizza! While the Berkshires boast many great pizzerias, Roberto's Pizza in Sheffield wins on both food and vibes. The fact that it's just a short stroll from Wilder House is a huge bonus! And with their fantastic new pub, we know you'll love enjoying cocktails and beers in their hip, modern setting. Plus, it’s super easy to grab carry-out and savor a delicious pizza in one of Wilder House's cozy dining areas. Hy’s Fried - South Egremont (Only 10 minutes from Wilder House) Craving something perfectly fried? Look no further than Hy's Fried in South Egremont! This vintage clubhouse, transformed into a lively bar and restaurant, serves up some of the best fried chicken north of the Mason-Dixon line. Don't even get us started on their incredible sides like fluffy biscuits, creamy potato salad, and cheesy mac and cheese! And as the evening rolls on, Hy's Fried transforms into one of the area's hottest spots for dancing, with live DJs spinning on Fridays and Saturdays. Get ready to groove! Juju’s - Great Barrington (Another 10-minute drive from Wilder House) For a fantastic lunch in Great Barrington, you simply can't beat the crunchy goodness of Juju's ! This locally owned popcorn chicken quick-service spot is a delight. With amazing wraps, fresh chicken salads, and creamy soft-serve ice cream, it's a fun place for the whole family and people of all ages. Plus, it's right in the same complex as the Triplex Cinema, so it's the perfect stop before your next movie! Cantina - New Marlborough (A scenic 20 minutes from Wilder House) Seeking a more upscale atmosphere in a wonderfully remote setting? Then you absolutely must check out Cantina in New Marlborough! Newly reopened, Cantina delivers amazing cocktails and a fresh, farm-to-table menu sourced locally from Mill River Farm. We especially love heading there on Taco Tuesdays for mouth-watering tacos and refreshing margaritas – it's a weekly tradition you won't want to miss! No. 10 - Great Barrington (Just 10 minutes from Wilder House) No. 10 in Great Barrington is another exceptional upscale steakhouse that consistently delivers incredible food. A guest once told me No. 10 is the best restaurant in America, and I'd say it's certainly in the running! If you're celebrating a major milestone or simply enjoying a romantic weekend, make sure you add No. 10 to your must-visit list. It also has the rare added benefit of being open seven days a week, which is a real gem in our region! Say hi to Jon at the bar (he's a friend of mine!) Once Upon a Table - Stockbridge (About 20 minutes from Wilder House!) Last but certainly not least, Once Upon a Table in Stockbridge is another tiny, hidden gem tucked away in an alley downtown. This charming spot consistently creates a warm and inviting environment with a menu that gracefully ranges from American classics to French and Italian influences. It's one of our absolute go-tos for a quiet, intimate date night that feels truly special. So, there you have it – a taste of our favorite culinary adventures in the southern Berkshires! Book a room at Wilder House today and let your taste buds thank you! 
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