The Wines of Woodstock: 5 Places to Sip Upstate

The Wines of Woodstock: 5 Places to Sip Upstate 1422 1376 Laura Harold

Arrive in Woodstock and drive down Tinker Street, the main drag in town. Through the string of kitschy shops offering tie-dye shirts, Persian rugs, and leather masks, you’ll notice guitar-shaped posts on the sidewalks that are endearing reminders of the bond between this town and music. One post in particular, standing about six feet high near the town center, sums up the vibe. In short, it reads: 50 years after the first, biggest end-of-summer party ever…come in peace to the town where it didn’t happen. (It’s true. Woodstock ’69 happened in Bethel, New York, about 50 miles south).

So, when Woodstock festival’s 50th anniversary concert was cancelled in 2019, the town remained unphased. With no shortage of local flavor to fuel the upswing of businesses here, true Woodstockers aren’t much concerned with it being a “happening” place, although it very clearly is. They know that the enchantment of Woodstock precedes their presence, and it will continue to exist long after they are gone—the charm that attracts so many to the tiny town and inspires creation in all forms. Here’s where to soak in the good vibes with a delicious glass of wine or two. 

Early Terrible

Tucked away in a small cabin on Mill Hill Road, I might’ve missed it if I didn’t see the mysterious signage posted on the sidewalk that reads “Early Terrible” in a chalky script, mastering the art of creepy-but-cool. Wander down a dirt path and head inside, where what I can only describe as a hip ski lodge makes you feel cozy but chic.

Doug Ballinger redesigned Manhattan’s Webster Hall in the 90s, and together with his sons Nicolas and Gray, opened Early Terrible earlier this year. Nicolas, who can often be seen bustling about the bar and greeting customers with conversation, tells me “You can kiss your girl here. You can talk to your mom. It’s a place for life’s moments.” I order a glass of Ermita de San Felices Rioja for $12, with a vanilla finish that pairs well with the warm evening. 

Early Terrible

The menu features some New York creations, with a Windham Vineyards carbonated white for 50 dollars a bottle or a Thin Man Burning Money IPA for eight bucks. The plates are small but not worth missing. Try their take on fish and chips with a salty smoked white fish mousse, smoked salmon, and crispy bread chips. Early Terrible is an orchestrated affair—from the music, to the food, to the people—the curations are indulgent but accessible. 

Station Bar & Curio

If Early Terrible were a piano prodigy who meticulously labors over each stroke of a key, then Station Bar would be your uncle, with a voice like Billy Joel, banging on the keys and having everyone sing along with him. I wait a few minutes to squeeze in at the bar where I order a glass of a 2018 Reserve Durand Sauvignon Blanc—a citrusy relief from the humidity. Glancing at another patron’s hot-pressed treat, I ask for a soft pretzel, too. They operate with a revolving menu based on what they have on-hand, from a chicken cordon bleu grilled cheese to the unexpected Bánh mì hot dog.

Perhaps Station Bar’s is an older sophistication, one that says, “Screw sophistication and be who you are.” Darts, pool tables, and an old piano underneath the covered patio are all adjacent to the bar, comprised of three joint rooms.

“We’re the caretakers here,” Ben Rollins, co-owner, tells me of the 119-year old abandoned train station that is now the bar. Woodstock resident Victor Basil hauled the thing 10 miles from Ashokan on his truck in 1970, which makes you wonder whether there is already a folk song written about this. Ever since, it’s been a casual meet-up spot for locals. Now it’s under the guardianship of Ben and his wife Lily Korolkoff, who decided to ditch NYC several years ago after driving through Woodstock with their four-month-old son and feeling inspired.

Station Bar

Taste more of upstate in their excellent beer selection. They have eight brews on tap and switch them up regularly. During my visit, this included a Chatham Ale Lager from Chatham Brewing and a Juicy Joy from Great Life Brewing in nearby Kingston.


A former buyer at Sotheby’s in London and then NYC, Gemma Bloxham was summoned from the city to move to Woodstock, and then, to renovate a property there that was an A&P supermarket in the 80s. Picture yourself buying tonic water off the shelf forty years ago; then see yourself today, sipping on gin and house-made tonic in the same space. The hand-picked wine selection includes a couple of standouts, too. Take the silky Wildekrans Pinotage, for example, a South African signature cross between Pinot Noir and Cinsault.

I inform the bartender I am in need of a dry red myself, and he provides me with a Napa Valley wine: the 2015 Cult Cabernet Sauvignon. As rich as it is subtle, it makes for the perfect standalone drink, though it wasn’t unaccompanied for long when my bangers and mash arrived. “Elevated comfort food with a European influence” is what Gemma calls their nontraditional versions of British classics.  

Thick English breakfast sausage links with hints of maple, made fresh from Woodstock Meats down the street, lay across creamy mashed potatoes completed by layers of brown gravy. To balance it out, you get a dollop of mint mushy peas and for added bite, a smear of the English classic, Colman’s mustard. A&P crosses genres for a mash-up, if you will, of international and local. 


Rosé Sparklers at Shindig

Find yourself in the Village Green and you’re likely to hear a drum beating, a guitar strumming, and the buzzing of the line outside Shindig during brunch. That’s what founders Ryan Giuliani (owner of the hotel Woodstock Way) and Allison Garskof (manager at Penelope in NYC) had in mind when they opened Shindig with a few colleagues back in 2015. There weren’t many spots for casual bites at the time, and their aim was to fill the gap. Just as a Buffalo Springfield melody starts up from town center, my wait outside is over when I accept a seat at the bar. 

This is a picture-perfect brunch spot—though they serve all meals—with a flair of its own and a stellar view of the mountains surrounding town. Two major players in Shindig’s cocktail selection are Prosecco and Soju (a Korean liquor similar to Saki but distilled from sweet potatoes). I try a Rosé Sparkler, a perky mixture of Fentiman’s Rosé Lemonade and Prosecco and a lovely start to my day, along with an order of fried Brussel sprouts with an avocado ranch dipping sauce.

The beers here are always local, like the Red Goat Farmhouse Ale from Arrowood Farms in Accord, or the Mother’s Milk Stout from Keegan Ales in neighboring Kingston. 

R&R Taproom

The cheese plate at R&R

Right off 375 and Mill Hill Road, this spot greets you the moment when R&R sounds like music to the ears of a road weary traveler. You might say the place’s charm mirrors its founder Megan Reynolds, a long-time gardener turned homebrewer turned certified cicerone, according the bar’s website. R&R has an open feel for a small space; its many windows let in warm light, there’s a shelf full of board games, Celtic open mic nights on Mondays, and a tiny, overgrown backyard. 

The bites are thoughtful, too. I order a cheese board with Nancy’s Camembert from Old Chatham Sheepherding Co., served with good sliced bread, nuts, fruits, and pickled watermelon rind (a delightfully briny addition) plus a fresh tomato and caper salad. I try some wine in my beer while I’m at it: Two Lights Italian Grape Ale from Portland, Maine, made with sauvignon blanc must, the freshly pressed juice of the grapes. 

Their selections are often updated, but a 2017 Seneca Lake Pinot Noir from Eminence Road in the Western Catskills is a homegrown winner from my time at R&R—a sweet and spicy New York state farm wine—proving that a full Woodstock experience needs no fanfare to sustain its flame. 

So, what if it’s the “town where it didn’t happen”? I’m convinced Woodstock is something that happens to you, anyway.

Laura Harold is a writer, artist, and editor for’s Family, Mind, and Fit sites. A wine and food enthusiast, she is enjoying opportunities to record her bar and restaurant experiences through travel writing, where narrative and critique form a perfect marriage. A graduate of Fordham University with a bachelor of arts in English language and literature and a focus on fiction, Laura currently resides in the capital of good food in NYC: Queens.

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