Why Woodstock, New York, is worth a road trip right now

Imbibe the eclectic, cozy vibes of this magical mountain town famous for its musical history.
Travel Woodstock
Here's how to explore the groovy town of Woodstock during COVID-19.TODAY illustration / Getty Images
/ Source: TMRW

Since March 2020, we've been adapting to life amid a pandemic. While many challenges arose, so too did creativity, inspiration and perseverance. A new sense of getting back to nature sprouted as many of us paused and appreciated the world around us.

To celebrate the many majestic communities across the U.S., TMRW is packing its bags and reviving the classic American road trip. Hop in the passenger's seat as we explore, eat and rest in Woodstock, New York. It's time to get on the road again.

The Woodstock sign at The Herwood Inn on Tinker Street in Woodstock, New York.Erica Chayes Wida

As a singer and artist who awoke daily to her father blasting songs from his 1960s record collection as a kid, Woodstock has always been on my bucket list. Despite its proximity to New York City and my teenage stint as a wannabe hippie, I've never been to the famously laid-back town. Now that I'm a mom living back on the East Coast, I thought what better time to go than when the musical mountain town is blooming in autumn.

So my husband and I took time off at work, halted virtual schooling, packed the bags for a two-night, three-day stay (which was plenty of time to imbibe the scenery) and took a road trip to breathe in some fresh air and soothe our stir-crazy, pandemic nerves.

Explore

Hike from a Tibetan monastery to deserted hotel ruins

Tibetan prayer flags line the pass along Meads Mountain Road.Erica Chayes Wida

Beginning at the Karma Tiryana Dharmachakra on Meads Mountain Road, we did the 4-mile hike on Overlook Mountain in the morning when the fog was so thick, we couldn't see much outside of a 20-foot radius. But the path was wide and clear, which made the uphill climb easy enough with two kids under 6-years-old (though I'd advise a hiking pack for toddlers).

This was one of the more mystical hikes I've done in my life, partly because of the weather and partly because we ended 3,000 feet above sea level with a colossal cement building coming into focus through the mist.

The Overlook Mountain House ruins stands in the mountains above Woodstock.Erica Chayes Wida

According to Hudson Valley Ruins, the abandoned Overlook Mountain House was first built in 1871 but burnt down four years later. It was rebuilt twice more, each time again destroyed by a fire until it was boarded up in 1940 when the new owner faced financial issues. It was perfect for a spooky October adventure, but on sunny days I imagine is quite beautiful with sky-high views of the Catskills from the lookout point just beyond the ruins.

Because of COVID-19, you can't visit the monastery but it's still beautiful from the outside and worth driving by if you don't complete the hike.

Kick back downtown

View of posters and signs on Tinker Street in Woodstock, New YorkAFP via Getty Images

Restaurants, cafes, juice bars, head shops, vintage clothing stores and record and toy shops speckle Woodstock's Tinker Street. At it's center, there's a New England-style white church and little square where tattered musicians play instruments for those passing by. If you stay downtown like we did, everything you need is in walking distance and certainly worth a nice stroll whether you're just window shopping or in the market for a new guitar or funky souvenirs. The theater housed in an old white house and the art gallery are closed due to coronavirus, but the public library is open with a big lawn covered in orange leaves.

Take in some tunes

A husband-and-wife band plays at Colony as the sun sets in Woodstock, New York.Erica Chayes Wida
  • The Bearsville Theater: This recently revived music venue set on 15 acres right on Tinker Street, which runs through the center of town, has recorded some of the greats from Bob Dylan to the Grateful Dead. Closed for years, the owner redid everything and was set to open just before the pandemic shut everything down. Still, she prevailed. Now open for outdoor jazz brunches, pop-up picnics, theater tours and live music every weekend, it's an ideal spot to revel in Woodstock's finest melodies.
  • Colony: Locals, families and music lovers fill up the large lawn filled with spaced out picnic tables surrounding an elevated stage. Red umbrellas with twinkly lights set the ambiance with the fiery Catskills mountains in the backdrop. The beer garden serves food, too, and features area musicians Wednesday through Sunday from 2 to 10 p.m.

Stroll through sculpture gardens

Depending on which way you're driving, there are two incredible sculpture gardens on sprawling acreage around Woodstock that are worth breaking up the trip or hopping back in the car to see.

  • Storm King - New Windsor, New York: About half-way between New York City and Woodstock, this famed sculpture garden has larger than life sculptures and contemporary art installations over its breathtaking 500 acres. To celebrate its 60-year anniversary this fall, the art center partnered with Ruinart Champagne to curate chef-paired picnics for two, which guests can purchase at the cafe in advance and take with them for a romantic fall date on the property. Because of COVID, people also need to buy tickets in advance. Storm King is open 10 a.m. to 4:30 p.m. everyday but Tuesday until December 13.
  • Art Omi - Ghent, New York: Fifty minutes north of Woodstock, this 120-acre sculpture and architectural park has free admission and is open daily from 9 a.m. to 5 p.m.

Eat

Silvia

Upscale American fusion with a menu fierce in umami dishes, this indoor-outdoor bistro had a dreamy ambiance, attentive service and a killer menu.

Mud club and Early Terrible

These sister-spots are situated on a big property on main street that not only looks like a fairytale woodland commune but is also ideal for social distancing. Open weekends only, Mud Club is a hub for wood-fired bagels and hot coffee in the fresh air.

Early Table, open Thursday through Sunday in the evenings, serves up funky cocktails and nibbles under twinkly lights and a roof made of tree branches so you can see the stars.

Yum Yum Noodle Bar

For less than $10, you can enjoy killer noodle bowls, bánh mì and crunchy fried chicken sandwiches with pickles and kimchi at this casual, no-fuss roadside spot. From outside, you can see the mountains while sipping a local or Japanese beer and devouring the lively dishes. The Korean barbecue pork tacos were out of this world (and I lightly consider myself a taco aficionado). While the ambiance is not much compared to some of Woodstock's other enchanting venues, the food certainly made Yum Yum a gem worth visiting.

Rest

The Herwood Inn is a magical, women-owned oasis in the heart of Woodstock's downtown.Winona Barton / @shelterupstate

The Herwood Inn

This artfully curated, queer-women-owned inn has made the top of my list of favorite boutique hotels from around the world. Opened last year by June Peterson and Em Atkins (then 24 and 22, respectively), each of the inn's four suites honor a female musician (Carole King, Joni Mitchell, Aretha Franklin and Stevie Nicks). Every nook is thoughtfully crafted, from perfectly stocked tiny kitchens to children's books about racism, tarot decks and games to eco-friendly cleaning supplies, cleansing sprays and a Herwood essential oil blend, which floats out of a diffuser and calms every nerve in your being.

Natural wood, white modern furniture and a mustard yellow chiminea balance the communal space, which is private for only the inn's guests who can relax in the cedar hot tub under string lights and lanterns or grab a free bike to cruise downtown.

Kid- and dog-friendly, the inn has taken many precautions to provide healthful comforts during a pandemic and was still able to maintain that quintessentially Woodstock feeling: peaceful, vibrant and liberating.

In addition to the Herwood Inn, other hotel properties in the area include:

  • Woodstock Way Hotel
  • Hotel Dylan
  • Foxfire Mountain House
  • The Graham & Co. Hotel
  • The Woodstock Inn on the Millstream