Your Field Guide to Woodstock, NY

Philip Mandelbaum
Jun 28 · 13 min read

Originally published at

As Your Local Guide to Ulster County and The Catskills, it is my honor and privilege to share with you all the best places to visit — from the the well-known tourist attractions to the hidden gems — in some of our most unique, interesting, educational and exciting cities, towns and hamlets.

For our June edition, I present to you the Nest Realty Co. official Field Guide to Woodstock, NY

Known as the “most famous small town in the world,” Woodstock is one of the most visited destinations in the Hudson Valley. A “Colony of the Arts” since 1902, Woodstock is the oldest operating Arts and Crafts Colony in America and, over the years, countless writers, poets, painters, actors and musicians have traveled here for residencies, festivals, recording, and teaching engagements.

Woodstock is heralded for its thriving, walkable town center, its music, theater, shopping, culture and world-class cuisine, and its proximity to awe-inspiring mountains, rivers, falls, watering holes and wilderness trails. In 2019, the town that inspired the original Woodstock Music Festival will be even more eventful, with summer and autumn celebrations of the 1969 music festival’s 50th anniversary, as well as milestone anniversaries of the Woodstock Artists Association and Museum, the Woodstock Film Festival, and the Center for Photography at Woodstock’s artist in residency program.

If you’re planning on househunting or weekending in Woodstock, be sure to bring this Field Guide with you.

Many travel guides offer tips on where to shop and stay, so in this Guide I focus on what I like to do: get outdoors during the day; and wind down with quality food and entertainment at night.

I’ve been visiting Woodstock for more than a decade, and I promise my picks won’t disappoint. Go #FindYourJoy!


“The spirit of the 1960s and early 1970s is still alive in Woodstock, New York. Peace, love, understanding, art, and music still reign in this quaint village nestled in the Catskill Mountains. There’s no better time to visit as all of New York State is getting ready for celebrations surrounding the 50th anniversary of Woodstock, the festival.” – I Love NY


Overlook Mountain
Meads Mountain Road
Woodstock, NY

Overlook Mountain is less about the hike, and more about the destination — and, believe me, it’s worth it. At the Village Green in the center of Woodstock, turn right onto Rock City Road. Continue past the four-corners intersection to Meads Mountain Road, and park in the lot on your right, approximately two miles down. The Overlook Mountain Trail is a moderate-rated walk on an old gravel path, with power lines overhead, yet Hike The Hudson Valley still awarded it its coveted five-camera rating for what lies ahead. Beyond the awe-inspiring Mountain House ruins, at 3,140 feet, Mt. Overlook features an historic 60-foot tower, built in 1927, with unbeatable views of the Hudson River Valley, Ashokan Reservoir, and Devil’s Path. In fact, the Overlook Mountain summit — blanketed by red oak, red spruce, and balsam fir trees — inspired many of artists who formed the famed Hudson River School and is today one of the top three most visited locations in the Catskill Forest Preserve. The trail is best used from March until November, and the cab atop the tower is open most weekends from Memorial Day through Columbus Day. Leash your dog, and bring her along!

Karma Triyana Dharmachakra Tibetan Buddhist Monastery
+1 845 679 5906 |
335 Meads Mountain Road
Woodstock, NY

Across the street from the Overlook Mountain parking lot is the Karma Triyana Dharmachakra Tibetan Buddhist Monastery, the North American seat of His Holiness Ogyen Trinley Dorje, head of the 900-year-old Karma Kagyu lineage of Tibetan Buddhism and guide to millions of Buddhists around the world. Located on 24 acres, the ornate monastery offers traditional teachings and contemporary programs, and hosts personal retreats, group visits and public tours. There is also an onsite gift shop, the Namse Bangdzo Bookstore, which, for more than 30 years, has stocked s a wide selection of Buddhist books, fine Tibetan Buddhist art, and Dharma practice materials. As it says on the monastery website, “All are welcome.”

Cooper Lake
Cooper Lake Road & Route 212
Woodstock, NY

Near Lake Hill in Woodstock is the largest natural lake in the Catskill Mountains, Cooper Lake, one of the most photographed locations in the region. For a casual wilderness walk, less than four miles from the Village Green, walk, bike or drive southwest on NY-212/Tinker Street and continue straight onto Wittenberg Road. Then, take a slight right onto Cooper Lake Road.

The Comeau Property
95 Comeau Drive
Woodstock, NY

A 10-minute walk from the Village Green, The Comeau Property covers 76 acres of meadows, woods and streamfront, protected since 2009 by the Woodstock Land Conservancy. The property includes a tranquil, minimally trafficked, dog-friendly (leash only) trail that parallels the Sawkill Stream for miles. Bring the kids, and park in the lot conveniently located opposite the trail head on Comeau Drive.

Woodstock Artists Cemetery
+1 845 679 4331
12 Mountainview Avenue
Woodstock, NY

The Woodstock Artists Cemetery is the site of the burial plots of many famous Woodstock creatives, including Jane and Ralph Whitehead, Hervey White and Bolton Brown, founders of Woodstock’s world-famous Byrdcliffe artists colony; 20th-century painters such as Philip Guston and Milton Avery; Frank Swift Chase, comedian Chevy’s Chase’s great-uncle and a painter who co-founded the Woodstock Artists Association; and Howard Koch, who co-wrote Casablanca. Many of the graves, themselves, are great works of art, crafted by Woodstock sculptors; and visitors to the Cemetery regularly spot the area’s living artists, “hoping to find inspiration among the graves of the inspired” (Atlas Obscura).

At Night

[In alphabetical Order]

“For many, the word Woodstock conjures up images of tie dye, hippies, and free love… That didn’t stop Woodstock from becoming a bohemian destination though… Woodstock’s ever-changing Main Street includes lots of new shops, restaurants, and lodging, making it a definite contender for the coolest destination in the Catskills.” – Escape Brooklyn

A&P Bar
+1 845 684 5395 |
83 Mill Hill Road
Woodstock, NY

Tucked behind a bank in the Sunflower market parking lot is the gorgeously designed modern rustic loft-style bar and restaurant known as A&P Bar. Known for its international comfort foods and artisanal cocktails, this hidden gem established in 2017 is fitting for families (in the lower-level dining room), date night (in the loft) or casual conversation at the dark-wood bar — where mixologists concoct custom cocktails like the signature Dawa, made from fresh-pressed apple vodka, with hints of fresh lime and mandarin, muddled with whipped honey. If you’re eating, we recommend the Flammkuchen, or German-style pizza, with forest mushrooms, gruyere and caramelized onions, and the shepherd’s pie, made according to an ancient English recipe.

Early Terrible
+1 845 684 7226
45 Mill Hill Road
Woodstock, NY

Heading northeast from the Village of Woodstock, down Mill Hill Road toward Saugerties, you can’t miss a stark black sign with the words Early Terrible scrawled in white. Down a path from the street is Woodstock’s newest hideaway, a sophisticated hipster wine bar with low lighting, exposed plank ceilings, antique windows and vintage flourishes throughout. (Your bill even arrives in an old book.) Led by Gray Ballinger — who helped open The People’s Pub in Chatham — and featuring a concise but eclectic high-end wine list, a selection of cocktail standards and a short menu of gourmet tapas, Early Terrible “embodies the new wave of Woodstock” (Chronogram) cuisine and culture.

Garden Cafe
+1 845 679 3600 |
6 Old Forge Road
Woodstock, NY

Looking out over the Village Green is the bright, airy Garden Cafe, the town’s 100% vegan restaurant where “food is medicine.” Serving breakfast, lunch and dinner, with two casual dining rooms, a juice bar and seasonal outdoor garden seating, the cafe uses only organic, non-GMO and cruelty-free ingredients, the highest-quality oils, and no preservatives, chemicals or trans-fats. Highlights include fresh-squeezed juices and made-to-order smoothies, specialty cocktails like the sake bloody Mary, menu staples such as the tofu satay with peanut sauce, scallions and orange-ginger slaw, and a blackboard full of daily specials. Eat here, and you might just go vegan yourself.

R&R Taproom
+1 845 684 5928
104 Mill Hill Road
Woodstock, NY

R&R Taproom was designed as a “‘third place’ — a social environment between home and work.” The casual beer bar and cafe near the center of Woodstock boasts a rotating selection of 10 draft beers and more than 50 bottled varieties, curated by certified beer sommelier Megan Reynolds, as well as a “vegetarian-friendly” menu of small plates featuring local, seasonal produce. With creekside dining, plus tastings, classes, workshops, popular “Youtube nights,” and Celtic Night every Monday, R&R offers a variety of educational opportunities, as well as a local safe haven for rest and relaxation (even though the R and R in the name is actually an homage to Megan’s grandfather and great uncle, who ran Reynolds Bar in the Bronx in the 1950s).

+1 845 684 7091 |
1 Tinker Street
Woodstock, NY

In the heart of the Village of Woodstock is the “easy-going eatery” known as Shindig, serving upscale comfort foods — made from local, organic ingredients — for breakfast, lunch and dinner. Recommendations include the Rock City Scramble, with scrambled eggs, havarti, chicken sausage and onion chutney; the Trout BLT, with grilled local trout, bacon, pickled onion, arugula and remoulade on peasant bread; the unbeatable hush puppies; and the milk and cookies plate.

+1 845 679 4242 |
42 Mill Hill Road
Woodstock, NY

With its gorgeous, oversized outdoor seating area and luxurious interior dining room with gleaming open kitchen and wood-fired grill, SILVIA strives to “connect food and people with back-to-basic cooking,” featuring fine farm-to-table cuisine from locally sourced, sustainably farmed, and GMO- and cruelty-free ingredients. The small but eclectic menu includes fresh breads baked on site from local, organic grains; a daily oyster selection; and mouth-watering entrees like the Trumpet Mushroom, with maitake and oyster mushrooms, spigarello kale, black garlic and parsnip puree, and crispy Jerusalem artichoke. This might be your favorite chef’s favorite restaurant.

Station Bar & Curio
+1 845 810 0203
101 Tinker Street
Woodstock, NY

A mere five minute from Woodstock’s Village Green, Station Bar & Curio is one of the hottest night spots in town. Serving some of New York State’s best local vodkas, gins, whiskeys and craft beers, this bar and lounge is known for its craft cocktails and beer flights, books and board games, outdoor patio, relaxed but stylish atmosphere, and regularly rotating collection of local arts and artifacts adorning its interior walls. Looking to snack? The “bar bites” menu changes often, but there’s always a hearty soup or stew, a seasonal hummus or pâté spread, and a gourmet grilled cheese sandwich with unpredictably perfect pairings.

The Woodstock Pub
+1 845 684 5470
17 Mill Hill Road
Woodstock, NY

Before the Landau Grill, which closed after 22 years in October 2017, what stood at 17 Mill Hill Road was The Woodstock Pub. Today, The Pub is back and, according to its new owners, lifelong Woodstock residents Jennifer Ahearn and brothers Chris and James Constant, it fills a void: the local watering hole, for locals, in the center of town. A few steps from the Village Green, The Woodstock Pub serves traditional pub fare, with a Mediterranean flair, and some exceptional surprises (like the gluten-free cheesecake creme brûlée!). If you’re looking for old-time Woodstock, quality food and drink, friendly staff and affordable prices, this is your answer.

[In alphabetical Order]

“This longtime artist colony (since 1787) was established around music, food, art, and eccentricity of all kinds; today the town stealthily retains a population dotted with a few big names, but also plenty of the coolest music industry people you’ve never heard of.” – Thrillist

+1 845 679 ROCK |
22 Rock City Road
Woodstock, NY

Housed in a stylish brick warehouse a short walk from the Village Green, the grand ballroom, performance space, cocktail bar and brand-new restaurant with stage and balcony seating now known as the Colony serves as downtown Woodstock’s home of rock and roll — and so much more. According to owners Neil and Lex Howard, both artists and longtime Woodstock residents, the historic venue has been lovingly restored and reopened “to encourage the exciting and creative energy flowing into Woodstock.” With weekly open-mic nights, comedy specials and regular appearances from the Rock Academy and traveling musicians of all genres (like the Meat Puppets on May 13, 2019), the proof is in the performances.

Levon Helm Studios
+1 845 679 2744
160 Plochmann Lane
Woodstock, NY

Also known as The Barn, the famous, cathedral-ceilinged Levon Helms Studios is tucked away, down a long unpaved road, on 18 acres in the woods of Woodstock. The American musical landmark, constructed in 1975 from local hemlock, pine and bluestone, was designed and acoustically engineered by The Band’s Levon Helms himself; it has served as home to Levon’s legendary Midnight Rambles, as well as intimate concerts, recording sessions, writing retreats and private events. Past performers include The Black Crowes, Mumford & Sons, Norah Jones, Guster, Medeski Martin & Wood, Natalie Merchant, Elvis Costello, Bruce Hornsby, Bob Weir, Phil Lesh, and many more. Performers in spring and summer 2019 include Ani Difranco, David Crosby of Crosby, Stills and Nash, and Jon Anderson of Yes.

The Lodge
+1 845 679 2814 |
20 Country Club Lane
Woodstock, NY

There’s history at The Lodge, dating back to the roaring parties at The Tea Room in the 1920s. Located on a sprawling, forested property down a long country road mere minutes from the town center, The Lodge features an intimate performance space and bar, attached farm-to-table restaurant focused on American comfort food, and separate “destination hotel” with nearly 20 rooms, standalone cabins and a new healted, saltwater pool with spillover jacuzzi. The team behind the revamp includes Brian Parillo, an alum of Levon Helm’s Midnight Ramble; real estate and development expert Michael Skurnick; product and design impresario Beth Bogulski; entertainment executive Jack Waterman; and chef Samantha Fernandez, from Wolfgang Puck’s New York City restaurant Cut.

Maverick Concerts
+1 646 965 2365
120 Maverick Road
Woodstock, NY

Maverick Concerts, Inc., is the oldest continuous summer chamber music festival in America, held in a magnificent, intimate “barn-like” structure with gambrel roof built in 1916 by writer and philosopher Hervey White. Celebrating its 104th year in 2019, the festival features renowned soloists and ensembles now performing chamber as well as jazz and contemporary music from June through September.

Woodstock Playhouse
+1 845 679 6900
103 Mill Hill Road
Woodstock, NY

An American theatrical landmark built in 1938 and rebuilt and reopened as a fully enclosed, climate-controlled, year-round venue in 2011, Woodstock Playhouse is a nonprofit theater that houses a variety of productions, festivals and events. Each year, the Woodstock Playhouse produces a celebrated summer season with its own professional company — “known as a stepping stone to Broadway” — and plays host to world-famous performing artists like John Sebastian, The Indigo Girls and Happy Traum. This year’s summer season features performances of Mamma Mia!, Newsies, Deathtrap, and Hair, as well as a Woodstock 50th-anniversary concert.


Did I Miss Your Favorite?

As you can imagine, Woodstock is deserving of (a lot) more than one visit — that’s why I visit every chance I get! As Visit Vortex explains, “There is a unique energy about Woodstock, NY. An energy that not only draws people in from all walks of life but gives the locals a sense of love and unity that can be hard to find in today’s world. Whether you’re searching for breathtaking scenery, ceremonial drum circles or just the good vibe, Woodstock has a little bit of it all.”

If you’ve got a suggestion that didn’t make my list, leave it in the comments!

Want to Be My Neighbor?

As an expert on everything Woodstock, Ulster County and the Hudson Valley, as well as a longtime REALTOR® and the licensed broker/owner of Nest Realty Co., it’s my specialty to connect my clients with the home of their dreams. I’ve done it many times before (just check the testimonials!), and I can do it for you.

Let me help you #FindYourNest:

Helen Coyle Bergstein
Broker/Owner, Nest Realty Co.
+1 845 417 7242



Philip Mandelbaum

Written by

Managing Content Editor, School of Motion | Director, Mandelbaum Marketing | Marketing Director, Opus 40 | Marketing Consultant, LTL MTN | Writer x Photographer