Activities for a Guys Weekend Getaway In The Berkshires

Sometimes you just have to get out of Dodge, especially when Dodge is actually your own hometown where your responsibilities are threatening to drive you a teensy bit nuts. When fresh air, excitement, and new surroundings send out their siren call, it’s time to gather up your very best dude friends and book a guys weekend getaway in the Berkshires. Here are all the things you can do once you hit hallowed ground in the lovely mountains of Massachusetts.

Embrace the Great Outdoors

Rack up a few thousand extra steps while enjoying a little friendly competition at one of the Berkshire’s many golf courses. Baker’s Golf Center is centrally located and offers both a 300-yard driving range and an 18-hole miniature golf course so there’s something for every ability level. More advanced courses are available at Bas Ridge Golf CourseBlandford Golf & Tennis Club, and Waubeeka Golf Links, among others, all of which serve up challenging holes and lush, well-maintained greenways. Should inclement weather make your outing all but impossible, grab your cooler and clubs and drive over to Downswing’s Indoor Golf Center, a PGA-recognized facility that boasts a whopping 100 golf courses programmed into each of their four simulators.

One the fairways are frosted over, recreation refocuses on the snowy Berkshire’s terrain. Skiing and snowboarding are popular pastimes here and there are numerous places to take your gang of guys. Ski Butternut has 110 acres of land and 22 trails ranging from newbie-friendly slopes to those intended for more experienced visitors. Berkshire East Ski Area adds tubing to the must-try activity list and you can also take part in lessons and night skiing. The trailside refreshments at Sloane’s Tavern make Cranwell Spa & Golf Resort’s 10 kilometers of groomer trails seem even more enticing but it’s the revving engines of the County-Wide Snowmobiling rentals that leave most macho visitors feeling very fired-up indeed. Grab your rented rides, head to one of the approved snowmobiling spots overseen by MassParks, and let the fun begin.

The Appalachian Trail weaves its way through Massachusetts, and more than ninety miles of the legendary footpath are situated in the western part of the state. While you’ll be much more comfortable safe and secure in your lakeside cottage at night, during the day you can head out for a day hike and experience one of our country’s most iconic walkways firsthand. The trail is only the beginning of the hiker-friendly routes in the Berkshires. You can hike and/or bike all around the region; choose Bartholomew’s Cobble for a gentle ramble through a natural rock garden studded with flowers and ferns, explore seven miles of trails and summit Lenox Mountain at Mass Audubon’s Pleasant Valley Wildlife Sanctuary, or aim for elevation on the network of winding trails high up on the wildlife-inhabited hills of Notchview.

Have an Adventure

What’s a weekend in the Berkshires without a little time in the sky? Berkshire Aviation Enterprises has been in charge of the Great Barrington Airport since 1944. They also offer flight training, with students sitting behind the controls from the very first lesson on. At Berkshire East Mountain Resort and Catamount Aerial Adventure Park, thrill seekers race through the foliage on zip line canopy tours that offer a squirrel’s eye view of the forest below. Want a little serenity with your ascension? You need to hitch a lift with Spirit Ballooning, the company that sends groups of 2-4 (don’t worry, you can charter multiple rides) up in hot-air balloons; gaze over the rolling hills, stately trees, and waterways below and learn to appreciate the Berkshires anew.

When you and your pals start feeling a little too hot and dry, see how it feels to have a bucket’s worth of ice cold water splashed mercilessly in your smiling face. That’s what it’s like to go rafting and kayaking down the dam-controlled Deerfield River, where Crab Apple Whitewater, Inc. and its energetic staff introduce enthusiastic rowers to the realities of the rapids. Or, if you can’t decide which risky endeavor you’d like to undertake, consider Zoar Outdoor; from rafting and kayaking to canopy tours and rock-climbing, this place does it all. A long day of challenging your limits and you’ll be more than glad to come home to your cozy cabin for a comfortable, full night of sleep.

Breweries, Wineries, and Beyond

The fertile land around the Berkshires has given rise to quite the agricultural community. Farmer’s markets and small country stores are plentiful, but for the purposes of a guys weekend getaway, the breweries and wineries might be a slightly more interesting use of the region’s crops.

The Berkshire’s boutique wineries bring world-class wine to Massachusetts. Visitors can tour the facilities, taste through portfolios, and purchase bottles for later consumption. Balderdash Cellars advertises “wicked wines & tall tales”, and that same penchant for wit is evident in wine names like the ‘Til Death Do Us Part Viognier and Truth Serum Albarino. Over at Hilltop Orchards’ Furnace Brook Winery, the vats are full of award-winning varietals like Cabernet Sauvignon, Merlot, and Riesling as well as ice wine and cider. There are tons of events on the orchards’ grounds as well in case you and the guys want to attend a Wax Clinic & Wine Tasting or a heritage hike. When learning about the winemaking process is as important as consuming the end result, visit Mary Jane and Wayne Eline at Les Trois Winery. The couple in charge are happy to give interested parties a glimpse at the magic before pouring out samples of selections such as Stingy Jack’s Pumpkin Wine and a soft and supple Shiraz-Cabernet blend.

Beer and liquor are also well represented in the Berkshires. Brands like Big Elm Brewing are demonstrating how delicious local microbrews can truly be by canning creamy stouts and hoppy IPAs that are both complex and refreshing. Their tap room is open for free tours and six-pack sales or you can bring a growler to serve later at your picnic. Bright Eyes Brewing also has a tap room or you can go straight for the hard stuff and add to the hair on your chest at Berkshire Mountain Distillers, Inc. The distillery churns out top-shelf spirits and the entire complicated process is on display at their Sheffield, MA, facility. Get your lesson in fermentation and then load up on small-batch vodka, gin, rum, bourbon, or corn whiskey; your haul will be excellent sipped beside a roaring fire later on or split up as souvenirs to act as a reminder of your epic Berkshire weekend with the guys years down the line.

Eat, Drink, and Be Merry

Man can not live on drink alone, which is why you’ll want a solid list of restaurants and bars before you head off on your guys weekend getaway in the Berkshires. Plan on a mix of cuisines, venue types, and price points. After all, variety is the spice of life and switching it up keeps things interesting.

Start your day with breakfast, brunch, or coffee and pastries – it’s your choice how you want to nosh in the early hours but you’ll definitely want something in your stomach so you have the energy to explore. Eating clean is always on the menu at the Starving Artist Creperie, an organic, gluten-free, vegan-friendly spot that specializes in delicate French pancake-like pastries stuffed with sweet and savory components. There’s live music on Sundays and organic brews from Barrington Coffee Roasters every day of the week. Hearty options come courtesy of Roses Restaurant; the floral wallpaper, curtains, and sprawling porch are a visual treat and you can’t beat huge omelets and stacked sandwiches at very reasonable prices. Chase away the previous night’s revelry with hot espresso, thick-cut smokehouse bacon, and pulled-chicken paninis at No. Six Depot. The café also does dinner and acts as a gallery for local artists interested in showcasing their work.

Pub fare is the name of the game at 20 Railroad Public House. The food menu is a tribute to local Berkshire purveyors and the cuisine is varied, interesting, and – above all – ridiculously tasty. Snack on curried cashews and Boston can bread, fill up on goulash and jaeger schnitzel, or cure whatever ails you with duck confit mac and cheese or spicy hangover hash. The chef-owned Aegean Breeze highlights the lighter side of Mediterranean eats with grilled whole fish, juicy gyros, and Greek-American tapas served in a room meant to mimic old-world indoor-outdoor dining. Craving something spicier? Depending on your mood, you can dive into Indian cuisine with a lake view and full bar at Mint, pass around paella and charcuterie at Mission Bar & Tapas, wash down ceviche and carnitas tacos with freshly squeezed margaritas at Pancho’s Mexican Restaurant, or tickle your taste buds with Thai-style curry and satay at Siam Square.

Then there are the bars. Some sling food alongside drinks while others concentrate on the entertainment aspect of Berkshire nightlife with live music taking center stage (literally). Thistle and Mirth is a dark spot perfect for anyone who wants to chill and chat with a craft beer on the table and chalk art on the walls. The line between wine and reading blurs at The Bookstore, an innovative yet charming spot that specializes in the best literary works as well as a surprisingly varied menu of reds and whites so everyone can “get lit”. Bet your buddies on the outcome of the big game at Mazcots Sports Bar & Grill; you can pony up a hundred bucks to support your team or just wager a basket of the bar’s addictive chicken wings.

When to Take Your Guys Weekend in the Berkshires

The mountains of Western Massachusetts are gorgeous any time of year, but you can make your guys getaway in the Berkshires even more special by scheduling your trip to coincide with another event.

  • 42nd Annual Josh Billings Triathlon: If your group contains a fair amount of dedicated athletes, consider signing up for this annual triathlon. As you bike 27 miles, paddle another 5 miles, then complete a 6-mile run to Tanglewood, you’ll get to take in the arresting scenery that makes the areas around Great Barrington, Stockbridge, and Lenox so revered.
  • Berkshire International Film Festival: Looking for less-active pursuits? The BIFF is a world-class gathering that features tons of independent, documentary, and short films along with the special events and panel discussions expected at a festival of this caliber. Use your guys getaway as an excuse to absorb some culture and see classic movies before the rest of the world gets their chance.
  • Lime Rock Park: Satisfy your group’s need for speed with a block of tickets to one of Lime Rock Park’s four annual races: the PWC Memorial Day Weekend, the IMSA Northeast Grand Prix, SCCA (Sports Car Club of America), and the Historic Festival on Labor Day. Depending on the race, you may see anything and everything from stock sedans to restored vintage rides to souped-up sports cars all zooming towards the checkered flag.
  • Hudson Berkshire Wine Festival: Foodies and oenophiles can fill up on local flavor at the Hudson Berkshire Wine Festival which takes place every May in Chatham, NY, a short 35-minute drive from Pittsfield, MA. Berkshire-owned family farms and businesses share their wares, offering patrons samples of delicious wines and spirits. In between sips, quell any stomach rumbles with hand-crafted snacks like artisan cheese, jams and jellies, and baked goods.

Start your guys weekend getaway in the Berkshires off on the right foot with reservations at The Lake House. Our luxury cabins hug the shores of beautiful Lake Pontoosuc, providing lovely views and plenty of space for canoeing, kayaking, paddleboarding, swimming, fishing, boating, and jet skiing. Fully-equipped kitchens and outdoor grills are perfect for burger and beer nights and we’re only a short drive to all the best attractions in the Berkshires. Ready to round up your gang and head for the hills? Drop us a line to buy out the resort or book a cabin or two for your crew today.