Looking for a  Berkshire County trail to take a hike with your honey?

We’ve rounded up some of our favorite hikes perfect for some grown-up time.  We’ve included spots to grab a bite or pick up picnic essentials. Scroll through and plan your next adult adventure!

Bob's Way | Monterey

FREE | 263 acres | Moderate

This BNRC property boasts wetlands, a beaver pond, and great birdwatching. Take Bob’s Way Trail (1.75 miles) until reaching the split at Cathcart Crossing. Steadily climb to Dave’s Bench — a sculpted-stone sitting area and enjoy the surrounding nature. Estimated Time: 1-2 hours. Leashed dogs okay. 

Suggested Pairing – Pack a picnic to enjoy at Dave’s Bench or stop at Naji’s or the Rio Cafe in Great Barrington for a delicious lunch you can take to-go or eat-in house.

Kennedy Park | Lenox

FREE | acres | Varying levels of difficulty

 Kennedy Park has many access points and parking areas. Less known is the tucked away parking lot just past the Church on the Hill as you head towards Route 7. Walking past a looming water tank, it’s a quick uphill to the picnic area and overlook that once was a part of the massive Aspinwall Hotel. From here you can extend your hike in many directions and lengths. Just be sure to pack a copy of the trail map! Estimated Time: Varies. Leashed Dogs Ok. 

Suggested Pairing – There’s no shortage of sights and restaurants in Lenox. Grab some breakfast at Haven Cafe & Bakery or an inspired and creative dinner at Nudel.

EXTRA WOW! Take a scenic drive down Undermountain Road and take in the picturesque views and scenery along the way. 

Mahanna Cobble | Pittsfield

FREE | 222 acres | Moderate to Difficult

This out-and-back hike of 3.2 miles can prove a bit strenuous with the elevation changes, but the payoff is certainly worth it! Take in the sweeping horizon and views from George’s Bench. Estimated Time: 2 hours. Leashed Dogs Ok EXCEPT during ski season.

**Because this hike shares property with Bousquet, be sure to check the BNRC website for trail guideline. Be aware, hikers use CAUTION during ski season and yield to skiers.

Suggested Pairing – Grab lunch at On A Roll Cafe just off of Route 7 (the pecan-crusted chicken caesar salad is YUM. Or grab a warm up and some sugar at Chocolate Springs Cafe

William Cullen Bryant Homestead | Cummington

FREE | 195 acres | Easy

Visit the home of writer and poet William Cullen Bryant and walk the trails that inspired much of his early verse.  Along the 1-mile Rivulet Trail, take in one of the rare surviving old-growth forests in and the additional Pine Loop to marvel at some of the tallest trees in the Northeast. Estimated Time: 1.5 hours.  Leashed Dogs Ok.

Suggested Pairing –  Grab sandwiches and coffee at the Old Creamery Co-op or extend your drive up Route 9 to the seasonal roadside stand Local Burgy for some alfresco eats.

Laura's Tower | Stockbridge

FREE | Moderate to Difficult (tower climb)

 Cross the fairytale bridge and begin your 1.5 mile round trip assent to Laura’s Tower. Climb the metal tower to take in views of the Berkshires, including Mount Greylock. Estimated Time: 1-2 Hours. Leashed Dogs ok.   

Suggested Pairing – Take a stroll through town and grab some pastries at The Lost Lamb Patisserie or grab lunch or dinner at the quintessential Red Lion Inn


Tourist Hotel Trails | North Adams

FREE / 80 acres / EASY

This riverside hotel harbors some unique woodland trails behind its smart exterior. Featuring a suspension bridge that spans the Hoosic River, dramatic meadow vistas and periodic art installations, this easy ramble in the woods will spark your curiosity and playful side. Although trails are open to the public, please be respectful of the hotel and its guests. Estimated Time: 1-2 hours. No dogs. 

Suggested Pairings – If you’re out and about in the morning, grab some grub from Brewhaha or picnic fixings from Wild Oats Co-op. For a delicious dinner before or after sunset, visit the Trail House Kitchen & Pub across the street from Tourists.

Hoosac Range Sunset Rock Trail | North Adams

FREE / 300 Acres / MODERATE

If you’re looking for wow-factor in the form of a vista and view, then the Hoosac Range is for you. A short but heart-pumping 1.6 miles out & back will lead you to Sunset Rock, an open overlook with views to the west and plenty of rocky outcroppings to watch the sun sink below the horizon. Just don’t forget the flashlights or headlamps for the way back down! Estimated Time: 1-2 hours. Leashed Dogs Ok.

Suggested Pairing – Open seasonally, The Wigwam Western Summit is both a sky-bar, coffee house, and gift shop all rolled in to one. Enjoy stunning views and a bite to eat before driving down the famous Hairpin Turn.  Or stop at The Golden Eagle Restaurant for a classic meal in a historic setting.

EXTRA WOW! While you’re in town, a stop at the neighboring Spruces makes for a great bookend to this outing. Once a mobile home community, this area is in the process of being revitalized as a public park. Just look for the hulking lions that guard the entrance!

BONUS: Make a Day of It!

Want to kick it up a notch and plan an epic day hike?
Tackle the highest peak in  Massachusetts and be rewarded with panoramic views of five states.

Mount Greylock Summit | Adams

FREE / 1,063 Acres / MODERATE to HARD

Hike to the summit of Mount Greylock via the Cheshire Harbor Trail. From the trailhead located at W Mountain Road in Adams, out and back trail to the summit is just under 7-miles. The shortest and easiest trail to the top, with a steady, challenging incline. Be sure to pack hiking essentials and include micro-spikes if hiking in the winter months. Estimated time: 4-5 hours. Leashed dogs ok.

Suggested Pairing – You’ll have worked up quite an appetite on this trek. If you’re okay with schlepping the extra weight,  this is a great location for a post-hike picnic before heading back down. Otherwise, hit up the Haflinger Haus to replace all that exerted energy. In the winter, you can even book a romantic heated hut!

Know a perfect hike that didn’t make our list? Drop us a line at taylor@berkshirefamilyhikes.com