Hidden in Plain Sight: Jivey Places for a Drink and Snack in the Southern Berkshires
By Jamie Larson
It’s always nice to be in on a secret, or two, or five. Southern Berkshire County is filled with amazing attractions, shopping, inns and restaurants, all classy places of deserved renown. But just around back, the region is hiding another of its virtues; some awesome classic taverns.
There’s a decidedly New England feel to these pubs, which are inconspicuous on the outside yet absolutely charming within. During a long fun day enjoying the area’s offerings, these watering holes are great places to duck into between engagements or in which to spend your evening. Each unique in its own way, these spots offer great drinks, top-notch grub, live music, and a whole lot of fun, right up until last call. If you like, you can hit them all in an evening—with some friends and a designated driver. They aren’t very far apart, and we’ve listed a lot of them here for those moments when you just want to hang.
Lenox is about as picturesque as a New England town gets and The Village Inn is an immaculate and sophisticated example of the region’s highest quality bed and breakfasts. But what if you want to let your hair down, put your elbows up, and throw back a few?
Well, head around back, down the snaking brick path to the small discrete red door of Rumpy’s Tavern. The passage is like a rabbit hole into an unpretentious dimension were the drinks are great and the atmosphere is light, even when the lights are low. With events almost every night, including DJs, comedians, live music Bingo, trivia and more, it’s the place locals and tourists alike go to unwind. And there’s food, from the upstairs Rumplestiltzkin’s Restaurant, including a surprising assortment of traditional Spanish tapas. Sure, they have a great burger, but there’s also the Spanish tortilla: a delicious egg, potato and onion dish that hasn’t caught on in the U.S. for some baffling reason. You can get a Catalan pizza on naan bread or a charcuterie board, too, and it’s all $10 or less. The Catskills can keep its Rip, the Berkshires has Rumpy’s.
16 Church Street, Lenox, MA
(413) 637-0020, ext. 385
Open every day, 5 p.m. – 1 a.m.
*Rumpelstilzkin’s Restaurant is permanently closed, but the bar remains open.
The Lion’s Den
The Red Lion Inn in Stockbridge, established in the late 1700s, is one of the most storied and venerated locations in the Berkshires. So it should come as no surprise that the Inn, with its classic rooms and beautiful restaurant also has a really cool historic bar in its basement. The Lion’s Den was built into the stone foundation of the Inn in 1937, and both the bar and booths are made of old dark wood, situated underneath a low red tin ceiling. It still feels like the 1930s down there: classic, tough, and sophisticated all at once. A visit to town wouldn’t be complete without a cocktail at the bar, backed by a mural of the red lion himself, holding court over his more common kin. The bar shares the Inn’s extensive wine cellar and kitchen, so you won’t feel left out just because you’re in the basement. The menu includes signature sandwiches such as the house roast beef with horseradish mayo, and smoked house-made hot dogs. There are also stellar specials, from pasta with Berkshire pork bolognese on Mondays to Lila’s Mt. Lamb shepherd’s pie on Saturday.
30 Main Street, Stockbridge, MA
Open Monday – Thursday, 4 – 10 p.m.
Friday, 4 – 11 p.m.
Saturday & Sunday, Noon – 11 p.m.
The Brick House
The Brick House in Housatonic is the only bar on this list that isn’t off the side of another business, but it is just off to the side of the normal route between Lenox and Great Barrington. Housatonic has a rough, industrial look, full of boarded-up buildings and ancient factories, and The Brick House had been the town’s no-frills local bar for a long time until it shut its doors in 2010. Now owned, reopened, and superbly renovated by a couple of former employees, The Brick House has gone from dive to gastro-pub for “beer geeks,” offering craft beers from the Berkshires, Brooklyn, and around the world.
This pub is the definition of a hidden gem. The large, rectangular island bar in the center of the place is intimate and encourages conversations between strangers. It’s a great place to watch a game, listen to a live local band, and eat food that is no less than a revelation. They have inventive burgers, an ethereal Philly cheese steak, homemade thin-crust pizza, bar snacks, a list of fries (including an order with truffle oil), and great lunch and dinner specials.
It just feels right at The Brick House, relaxing and friendly. Get off the main road and onto a bar stool that you’ll find yourself hesitant to leave.
425 Park Street, Housatonic, MA
Open Monday – Thursday, 4 – 9 p.m.
Friday & Saturday, 11:30 a.m. – 10 p.m.
There’s a strange, beautiful harmony between the sound of ice clinking in a glass and the clatter of a bowling ball scattering pins. A bar in a bowling alley is an amazing place to be, completely out of the way as the world goes on around you. At Cove Lanes in Great Barrington, you can take a break from a game at the bar or make the bar your destination.
Cove has a real understanding of what you want in a bowling alley: distraction, games and family fun, but also ambiance. From its vintage, iconic roadside signage to the sweeping mural of the mountains above the lanes, Cove is a caught-in-a-moment real-time experience, especially from the bar stool.
It might not be your first thought when it comes to grabbing a beer and some quick food, but that’s what makes it great. Getting off the beaten path and out of the routine is therapeutic. So grab a burger, sandwich, or hot dog at the bowling alley and pretend you’re Zen like “The Dude.” The Cove feels like a portal into the The Big Lebowski, and if you’re on a budget it’s the place to be, with $1 PBRs. Try it, and heck, bowl a frame while you’re at it.
109 Stockbridge Road, Great Barrington, MA
Open daily, 9 a.m. – Midnight
Friday & Saturday, 9 a.m. – 1 a.m.
Cosmic Bowling, 9 p.m. – 1 a.m.
Down County Social Club
Only open on Thursday nights, the DCSC is tucked into the basement of the elegant and highly praised Stage Coach Tavern in Sheffield. The Club offers live music and other performances in the little hideaway to the 20 or 30 people that can cram themselves in. There’s a timeless speakeasy feel to the joint and, with everyone so close, there’s an energy unmatched by larger venues (which is pretty much any venue).
Enter through an old wooden door on of the side of the tavern and descend into a little pocket of artistic heaven. They serve wine and beer down in the Social Club, but there’s also the full Tavern bar upstairs alongside some phenomenal food. Grab a bite upstairs in a calm moment before descending into the magic den hidden beneath your feet. Upstairs they serve steaks, seafood, pasta, incredible salads, and much more, all with a moral compass pointed towards the local food movement and farm-to-table dining.
Downstairs in The Social Club it’s just that, social, friendly, and open to everyone from regulars to upstairs guests who didn’t know the club existed until they happened by on a Thursday. And how lucky they were to come for dinner and stay for an unexpected dream sequence.
864 S. Undermountain Road, Sheffield, MA
Open Thursdays, 8 – 11 p.m.
No cover; suggested donation.