The best place to see live music in New York is actually upstate

This article is part of FT Globetrotter’s guide to New York City

I navigate down an unmarked road, our Subaru crunching through the snow. A woman outside a kiosk checks my name off a list and I’m waved into a parking spot. I pour a beer into a cup — a Kölsch from nearby Kingston Standard — and start the short trudge to the venue. I walk past a campfire and a garage that’s now a merch store, up the steps and inside, no metal detectors in sight. We’re here: Levon Helm Studios, a place that everyone around here simply calls The Barn. Tonight’s show is the annual tribute to Gregg Allman of the Allman Brothers.

Everyone here seems to know each other, from showgoers to staff members. Security smile as they guide patrons to their seats in the barn’s balcony, among the eaves. This structure was built in the 1970s from local hemlock, pine and bluestone. Remarkably, no one here appears to be checking their phones.

A two-hour drive upstate from Manhattan’s Madison Square Garden is a region of the Catskills awash with theatres, bars, repurposed barns and outdoor spaces. Instead of wrestling to the front at Webster Hall in Manhattan, or battling a virtual queue for $600 nosebleed seats, this is a place where you can relax, and music will practically come to you.

I have travelled to Zürich to see Metallica in a football stadium, San Francisco for last year’s Dead & Company farewell shows, and London to see Liam Gallagher play The O2. But when my wife and I drove upstate with a friend for an easy weekend in Woodstock, we realised our Airbnb was across from Bob Dylan’s old home. We couldn’t resist the town’s combination of natural beauty, artistic spirit and music history, and ended up moving here part time. This area, in my opinion, is one of the best places to see music in the world. You get the sense from the quality of the acts that musicians prefer it to the big cities, too: studios abound, and REM, Dave Matthews Band and more recently The Lumineers have decamped here to record.

The town of Woodstock isn’t exactly where the famous 1969 Woodstock festival took place — that’s about a 90-minute drive away. But it’s still a town whose musical history seeps into you, even if you’re trying to avoid it. Take a highway into town renamed for Levon Helm, the late drummer, singer and mandolin player of The Band. Eat at the trendy farm-to-table restaurant Silvia, and feel the ghosts of The Rolling Stones, Muddy Waters and Phish who played in its former incarnation, Joyous Lake. It even comes alive at the local Bread Alone bakery chain; splashed across its walls are images of The Band taken by photographer Elliott Landy. Landy still lives in town. (You can see some of his photographs in this guide.)

Woodstock and nearby Kingston and Saugerties are loaded with places to experience live music in cosy surroundings. Here are some of my favourites.

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For a midnight jam: Levon Helm Studios

160 PLOCHMANN LANE, Woodstock

Levon Helm designed and acoustically engineered The Barn in 1975, a year before The Band played its final star-studded concert (Martin Scorsese captured it a few years later in his film The Last Waltz). When Helm’s health declined in the early 2000s, he started hosting Midnight Rambles — loose performances where musical friends joined him onstage, surrounded by a packed crowd, to sing songs they loved.

The musician’s daughter Amy Helm, a singer-songwriter in her own right, now owns and runs The Barn. She told me that only 20 people showed up for the first Midnight Ramble, but it quickly became an institution.

“People love to see something unique, and bands like to play a room that has history,” she said. “The Barn is a room, built by a drummer, for musicians. It’s also a room where [my dad] completely overcame throat cancer, bankruptcy, drug addiction, all rolled up into one — he played his way up and out of it with no visions of grandeur and, frankly, no success at the beginning.”

Many musicians consider The Barn hallowed ground. The acoustics are exceptional. If you can’t make a Midnight Ramble, the venue also hosts touring acts.

• FYI: Midnight Rambles start at 8pm, not midnight. Almost all shows sell out, so get your tickets in advance from the venue’s website. You can also sign up to be a “Barnburner” member and get access to tickets before the general public.

• Website; Instagram; Directions

To see big-time touring acts in a small-town theatre: Bearsville Theater

291 TINKER Street, Woodstock

Two miles west of downtown Woodstock, Bearsville Theater is part of a campus that includes a studio, restaurants and a garden where occasional small music festivals are held. The space is intimate but not cramped, with a large lobby and high ceilings. You can even get a clear view of the stage, with great sound, from the lobby bar. 

I recently saw one of my favourite artists, the pianist and singer Bruce Hornsby, here. He played a song with the opening act, a younger jam band called Eggy, and then Eggy members joined him during his.

This theatre is also hallowed ground. It was built in the 1960s by Albert Grossman, who managed Bob Dylan, The Band and Janis Joplin, as part of a creative hub that also included a studio. You can visit Grossman’s grave in the garden.

These days, the venue is run by music entrepreneur Peter Shapiro and his company Dayglo Presents, who also operate Brooklyn Bowl. Shapiro tells me the demographic is people who like escapism and culture: from “bearded hipsters, to urbanites in their thirties and forties to grey-haired hippies”. 

Musicians of all stripes have used this space for special events. The National recorded a concert film here. Pop star Shawn Mendes debuted his album here in 2024. This is the place to see underplays, or well-known artists playing smaller venues than usual.

• FYI: Sign up to email alerts on their website so you don’t miss an underplay. If you manage to snag tickets, show up early enough to have dinner at the excellent Bear Cantina Mexican restaurant or Tibet Pho, or grab a drink at the Tinker Street Tavern, all on the campus.

• Website; Instagram; Directions

For classic rock in a charming old hotel: Colony 

22 Rock City ROAD, Woodstock

With high ceilings, a wraparound balcony and hanging string lights, the former Colony Hotel — which calls itself “the smartest rendezvous in the Catskills” — is worth your visit. The vibe sits somewhere between speakeasy and ballroom. Downstairs, you can sit at tables, stand, or take the grand staircase to the balcony. (Sadly, you can no longer stay here overnight.)

At Colony, tribute shows abound, with the last Wednesday of every month a committed Grateful Dead night. They also have plenty of original acts playing Americana, blues and rock. Some of my favourite recent Woodstock musical moments have happened here, like indie singer Soccer Mommy covering the Slowdive song “Dagger” and Professor Louie and the Crowmatix’s tribute to his old friend and collaborator, Rick Danko of The Band.

• FYI: The kitchen pumps out delicious chicken wings, fish sandwiches and nachos. An outdoor beer garden with live music is open in the spring. 

• Website; Instagram; Directions

 

For venues you don’t expect to be venues: Kingston, New York

Various

Drive for less than 20 minutes from Woodstock and you’ll reach Kingston, a small city with an interesting history. Kingston was New York state’s first capital under the English in 1777, and prominent structures from its colonial era still stand, like the Old Dutch Church and the “Four Corners”: the only intersection in America where the buildings on all four corners were built before the Revolutionary War. Kingston has a great food scene, and though there are fewer live music venues here than in Woodstock, I advise a visit.

Its newest entry is Assembly (236 Wall Street), the former auditorium of a 1912 schoolhouse in the colonial Stockade District, with a capacity of 450. Walk into the old St Joseph’s Catholic School, climb the stairs, and you’ll find what looks like a high-school stage, complete with arched windows, exit signs and a restored ornamental ceiling. Though it still has the nostalgic look, the improved acoustics make it sing.

When I visited, partner and co-founder Drew Frankel introduced me to comedian Ashley Gavin before her sold-out performance. He told me that the room is filling a void: until it opened at the end of 2023, acts looking to play a medium-sized venue were out of luck. Assembly will host Dirty Dozen Brass Band in the spring.

Step into Tubby’s (586 Broadway) in Midtown, and you might not even notice the small stage in the back room. But the corner bar boasts a music calendar to rival a big-city club, with recent visits from well-regarded indie groups like Black Midi, Shabazz Places, Steve Gunn and David Longstreth of Dirty Projectors. The indie, alternative and electronic music attracts a younger and hipper crowd that is more Williamsburg than Woodstock. 

• FYI: Beer aficionados should visit West Kill Brewing’s Kingston Taproom (602 Broadway, Unit 2), a two-minute walk from Tubby’s, for an eclectic offering of beers and an only-in-the-Catskills aesthetic featuring animal taxidermy and tap handles made from antlers. 

You can read more of our New York City guide here, including a film lover’s guide to the city, Danny Meyer’s tour of Union Square, the city’s best barbershops and women’s shoe shops, food tours of Flushing, Queens and Red Hook, Brooklyn, and winter getaways in the Hudson Valley

Where are your favourite music venues, in and around New York? Tell us in the comments below. And find us on Instagram at @ftglobetrotter.