Berkshires After Dark: Late-night haunts for night owls


"After dark" is not, in practice, the fixed time frame that it so often seems confined to around these parts. I'm confronted with this reality every weekend or two while visiting my girlfriend in New York City. Streetlights and open doors spilling music onto the sidewalk invite me to explore the whole grid by foot at 3 a.m., when the rushing city rushes my thoughts out the door while most of you slumber.

There is little distinction on these streets, though, between evening and morning, the close of one day and opening of another, due to a mish-mash of millions of overlapping schedules or not-schedules. And despite decades of Richard Linklater's efforts, science is no closer to explaining how and when we can distinguish a precise moment of changeover from sunset to rise.

Bringing this formulation of "after dark" back home helped sift out some surprising places of congregation open long after our state's blue laws shoo all the crowds apart. But this poses the risk of the Winthrop Wallop to any night owl looking to carouse along the promenade: a 1633 state statute, still on the books, advises constables to identify those "spending their time idly and unprofitably" and to "take knowledge of offenders in this kind, especially of common coasters, unprofitable fowlers, and tobacco takers."

I'd protest, but to be honest I've never turned a profit in fowling. My point is that almost all the local businesses, and this includes the paved spaces and scenery-swallowing infrastructure surrounding some of them, close down at 5 or 7 or 9 p.m. and shut off the lights.

As 4 a.m. Brooklyn streets bustle with movement and conversation, our towns develop their own bug lamps that attract a critical mass of buzzing customers who come by regularly and, in the best cases, develop a friendly relationship with the staff and each other. I saw this when I worked at a cafe on the morning shift, I saw it serving drinks from dinnertime until 1:30 a.m., and now I see it frequently at 24-hour convenience stores and supermarkets, though on a much smaller scale. Mention of these after-dark staples is long overdue as they provide otherwise unavailable services to nighthawks, as well as more socially oriented sleepers up late or early, in our small towns. That can make a big, big difference.

Dunkin' Donuts on First Street, Pittsfield, is the sole fast-food alternative I'm aware of within county lines. Waves of people in their teens and 20s and smaller groups of all ages come through the place after dinnertime, some rumbling up in cars and roaring in on motorcycles, others on skateboards and bicycles and on foot. The ever-refreshing scene of people sure slows down in the wee hours, but nonetheless exists and is thus noteworthy.

O'Connell's Convenience Plus at 265 Housatonic St., Lee, is exemplary of the unspoken social needs that a business -- any business with access to space -- can provide, whether by dint of skillful management or by proximity to the right place and time. I don't need to tell you what a Convenience Plus is like, but the Lee outfit features the most jocular late-night staff I know.

My regular patronage was founded years ago on its ready-to-go microwave slices and chicken wings that were surprisingly delicious. Sandwiches and potato salad are made of ingredients noticeably fresher than those of comparable businesses (there is an in-store deli) and actual fresh fruit, Nothing fancy, but nothing substandard, either. I once spent three midnight hours there when a blown tire found my car flapping to a halt in the gas station's parking lot and AAA was MIA or AWOL. I was SOL but D4W. NBD.

At Cumberland Farms at 140 Main St., Great Barrington, I routinely encounter a younger crowd, some of whom hang around listening to music and meeting, flirting, formulating plans. The Cumby's at 145 First St., Pittsfield, draws a steadier crowd of all ages with a little more weight on the "middle age" demographic, if that still means anything, and can become quite the popping little scene on a midsummer night. But the eclectic and mostly adult crowd displays a volatility I don't see elsewhere. People vent more at the Pittsfield store. Price Chopper in Lenox is the best thing going in terms of menu (everything), spaciousness (it's staged in a blimp hangar) and seating (a quiet and nearly private dining area containing high-backed booth seats and free-standing tables with chairs, much like a classic diner). The deli and hot food counter close after dinnertime, but the store sells plenty of daily prepped meals and snacks that can make for a lovely meal on the spot. I once led a well-fated date to this supermarket food lounge. Big hit! Appreciation of kitsch a must.

As with Convenience Plus in Lee, this Price Chopper stands out to me as a bona fide social outlet for night owls who wish to integrate other people into their figurative daily routines. I sense a unique tone in the social atmosphere of this store -- subdued, playful, and professional -- and can't help but trace its roots to the staff.

Whatever the cause, community and communication happen there. I encounter it each time I enter Citgo at 55 Housatonic St., Lee. True, there's not much variety between convenience stores, but this round-the-clock shop is a place where people dawdle for far longer than necessary to join in on whatever interesting conversation comes to the counter. I see an older crowd here and like it a lot. The employees have exceptional memories, too: two clerks individually spotted me parking, remembered my usual order, gathered it on the counter before I walked in and greeted me with a wide grin.

Exit 2 on the Pike steers a car into downtown Lee, so businesses that cater to a mobile and all-hours customer base have flourished and remain in operation. This gives the town its locally uncommon strip of fast food chains, motels, gas stations, and family restaurants.

Our rating

Rating: Varied (see below)

If you go ...

Style: Anything open 24 hours in the Berkshires

Dress: I wouldn't worry about it

Cover: No

Food: Mostly processed foods, though health-conscious eating has becpme a much larger presense in recent years.

Entertainment: Some of these places provide a social forum in which people interact nightly when there's seemingly nowhere else to congregate.

Our rating: 1 mug, Run away; 2 mugs, Yawn; 3 mugs, Cheers; 4 mugs, "I'll be back"; 5 mugs, "Round's on me!"

Your rating: You can rate these businesses at

Tonight's roundup:

Citgo, 55 Housatonic St, Lee: (413) 243-6443. Laid-back convenience store with a more mature crowd. Decent beer selection for a tiny mart. Very cool employees. 3 mugs, Cheers.

Cumberland Farms, 140 Main St, Great Barrington: (413) 528-2105. Younger crowd, more energy in the parking lot and store, recently refurbished and expanded to become quite a large little shop. 2 mugs, Yawn.

Cumberland Farms, 154 1st St, Pittsfield: (413) 443-4478. The busiest gas station mart on my list, there's no predicting what atmosphere you'll step into. Sometimes stoic or dull, other times wisecracking and gregarious, and just as often fraught with tension coming from someone who walked in there ahead of you, this is my least favorite of these places to spend time. 1 mug, Run away.

Dunkin' Donuts, 18 1st St, Pittsfield: (413) 499-0371. The crowd reliably changes throughout the day and night, but rarely feels inviting tor invigorating to me. 2 mugs, Yawn

O'Connell's Convenience Plus, 265 Housatonic St, Lee: (413) 243-2408. Funny fellas at the counter, a good humored crowd and some tasty and healthful food options. 4 mugs, "I'll be back."

Price Chopper Supermarkets #233. 495 Pittsfield Rd, Lenox: (413) 443-5449. Try grocery shopping very late at night sometime. A peaceful shopping experience that you've only glimpsed in shampoo commercials is real and awaiting your participation. 4 mugs, "I'll be back."


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