Blake Walsh

25 Best Things to Do in Woodstock, NY

  • Published 2023/01/19

New York comprises innumerable towns and cities, each of them unique and culturally active in its own sense.

They are not interlinked; all of them stand as separate entities.

One such town is Woodstock, which is more of a village and township.

The town is devoted to art, with a low-key atmosphere and many exciting things to do.

Interested to know more about this place?

Here are the 25 best things to do in Woodstock, New York:

Take a Stroll on Tinker Street

Tinker Street in Woodstock

Beyond My Ken, CC BY-SA 4.0, via Wikimedia Commons

Head to Tinker Street, Woodstock’s most enjoyable place to stroll and shop.

The street is always sprawling with people, and the shopkeepers are keen to show you the best.

Exterior of a bed and breakfast house at Tinker Street

Beyond My Ken, CC BY-SA 4.0, via Wikimedia Commons

There are art pieces displayed on the walls, making every corner picture-perfect.

You can catch hold of some vintage postcards, personalized apparel, and customized jewelry to take back home.

Pray at the Holy Transfiguration Church

Exterior of the Holy Transfiguration Church

Dmadeo, CC BY-SA 3.0, via Wikimedia Commons

The Holy Transfiguration Church is modestly beautiful.

This tiny church holds a massive religious significance.

Located in between the woods, it is an aesthetically looking edifice.

The architecture is old and Victorian.

Decorated with the infamous stained glass windows, this church is beautiful.

This is a more offbeat location as it is not visited as much as others, but it deserves much more recognition.

The church is always open to devotees.

There is a baptism pool attached to the shrine, too.

Catch a Show at the Bearsville Theater

Bearsville Theater is a renowned theater in Woodstock.

Every person who visits this place ends up in awe of the shows presented.

It is probably the best venue to watch a show.

They have got the best band in the town.

Keep your eyes open for some new show or gig.

It will be a fun and worthwhile experience here.

Catch a Show at the Woodstock Playhouse

Exterior of the Woodstock Playhouse

Beyond My Ken, CC BY-SA 4.0, via Wikimedia Commons

It is said that Woodstock is famous for music and art, and Woodstock Playhouse is the most proper place to understand and get to know Woodstock’s music scene.

Many musical dramas and theater plays take place in the Playhouse.

Located right on the main road, it is easy to find.

The seating is comfortable, and the lights set just the right mood.

The artists performing here are top-notch and highly skilled.

You’d love any show you choose to watch.

All of them are equally amazing and worth the time.

The energy of the artists onstage is contagious.

The audience gets filled with zeal and happiness, too.

You’ll feel like you are on Broadway, even though you’ll be sitting in Woodstock.

That’s the kind of enthusiasm and stage show this theater holds.

Attain Solitude at Karma Triyana Dharmachakra

Colorful interior of Karma Triyana Dharmachakra

Michael Pawluk /

Karma Triyana Dharmachakra is a Tibetan monastery located in Woodstock.

It is open to everyone, not just Buddhists.

The monastery serves as a retreat center.

If you are looking for a peaceful escape from the city, this is your spot.

Exterior of Karma Triyana Dharmachakra

Michael Pawluk /

The spirituality of this place is pure and composed.

You can meditate or gather your thoughts by taking deep breaths.

The atmosphere is charged and calms your mind instantly.

Regardless of what you believe in or worship, it would be best to visit this place.

Buddhist statue in Karma Triyana Dharmachakra

Michael Pawluk /

Visit Mower’s Saturday Sunday Flea Market

Flea markets are always fun and vivid.

Mower’s Saturday Sunday Flea Market is no different from that.

You’ll find everything here.

They have the oldest collections and everything new and trendy as well.

If you are fond of vinyl records, you can grab some classic records here.

There are different items every week.

You’ll get a lot of varieties to try and select.

It would be best if you browsed through many stalls and vendors to find suitable items.

Snacks are available if you feel hungry in between your shopping spree.

The vendors are friendly, and they do negotiate the prices.

You don’t need to spend a lot of time here; you can give glance and get your desired things.

Be sure of your choices, and you will get your hands on the best of the best.

Go shopping in the morning—it will be calmer and less crowded.

Have a Delectable Bite at Bread Alone

Read Alone serves fresh and scrumptious bakery items.

They have assorted pastries, including mouth-watering cupcakes, croissants, and cookies.

Bread Alone also brews dark and creamy coffee.

They add the perfect amount of sugar and top it off with whipped cream.

Listen to Live Music Anywhere

Drum circle gathering in Woodstock

littlenySTOCK /

Quite literally, you can listen to live music anywhere in Woodstock.

Music is etched into the town’s soul, which is evident from the vibe you get there.

A drum circle at Woodstock

JWCohen /

Every corner has someone or the other playing an instrument or humming a tune.

You should venture out in the streets at night because the atmosphere is lively and many people will be strumming some fantastic tracks on the road.

People dancing during a drum circle

JWCohen /

Stop by the Sun Frost Farms

If you are looking for farm-fresh products, Sun Frost Farms must be your go-to place.

They sell exotic and fresh produce.

You will get a lot of vegetables, fruits, bakery items, and dairy products here.

The veggies are locally grown and delivered right from the farm.

Gourmet items and baked dishes are worth spending on.

Also, there’s an eatery that serves juices and salads.

Check Out the Woodstock Artists Association & Museum

Exterior of Woodstock Artists Association & Museum

ajay_suresh, CC BY 2.0, via Wikimedia Commons

Woodstock Art Association and Museum, or WAAM for short, is a cultural center in Woodstock, New York.

This art gallery has supported artists, building and fostering collections, providing educational programs, and giving back to the community since 1919.

Over a hundred years of history, WAAM has acquired an impressive and diverse collection to provide visitors with a comprehensive overview of current trends and historical precedent in the visual arts.

The Woodstock Arts and Music Association sits in the center of the touristy town and functions as a cultural center and a public gallery for regional artists.

Artists associated with the Art Colony exhibit their work here each year.

Each day, this contemporary treasure features a variety of visual art exhibitions inside its five spacious art spaces.

Get Tickets to a Show at the Byrdcliffe Theatre

Surrounded by forests, Woodstock Byrdcliffe Guild is a lovely 250-acre center for artists, and a premier destination for creative minds found up in the Catskill Mountains.

The grounds are a peaceful and serene escape from the urban bustle, consisting of beautiful greenery, trees, cabins, and even an art gallery.

This award-winning facility provides an integrated program of studios, theater, exhibitions, classes, concerts, performances, workshops, and artist residencies.

At the Woodstock Byrdcliffe Guild, you’ll find a small comfortable performance space with an intimate setting known as the Byrdcliffe Theatre.

This intimate theater space offers a wide variety of dance, musicals, and other performances meant to give you the most enjoyable Woodstock vacation.

If you want to get away from it all or want to soak in the beauty of nature while still enjoying modern life’s amenities, then the Woodstock Byrdcliffe Guild may be just what you need.

Take a Load of Memorable and Unique Photographs of Woodstock Waterfall Park

Scenic view of Kaaterskill Falls

yggdrasill /

With so many impressive outdoor destinations to choose from, one might miss the hidden waterfall known as Kaaterskill Falls of Woodstock, New York.

Nestled just north of one of the town’s main thoroughfares is a small but charming waterfall park in Woodstock.

This quiet and quaint area of land is a local favorite for people looking to enjoy one of Woodstock’s most tranquil views.

The site is named after its striking views on Tannery Brook as it cascades over the rocky stream bed into a small but deep pond at its base.

Woodstock Waterfall Park is a significant hidden landmark when you find yourself in Woodstock or passing through the Catskills.

This is another perfect place to take memorable and unique photographs!

Drop by Woodstock Music Shop

The Woodstock Music Shop is an all-in-one shop for vinyl records, musical instruments, accessories, and other similar bits.

Along with the music store, they are also available to impart the fascinating history of music, its cultural scene, and other helpful stuff.

The 500-square-foot shop was formerly a bank and featured an actual vinyl vault stocked with thousands of records.

They sell new and old vinyl, secondhand instruments, gear, and handcrafted vinyl art.

Every year, Woodstock Music Shop participates in Record Store Day.

Drop in and explore the Woodstock Music Shop, open daily from 11 a.m. to 6 p.m.

Pamper at Glo Spa Woodstock

Among the various services offered by Glo Spa are top-notch facial treatments, soothing massages, and revitalizing body treatments.

Glo provides amenities comparable to those at a five-star hotel and the finest luxurious treatments.

Customers can enjoy the steam room, infrared sauna, guided meditation O2 chair, magnificent retail shop, and a breathtaking view of the Catskill Mountains throughout the year.

Visit Glo Fitness, the only deluxe gym in Woodstock with exercise equipment, weights, fitness programs, and showers.

Don’t forget to swing by the Glo Shop before you leave; the best skin care items, cosmetics, and gifts are offered here.

Have a Delicious Meal at Cucina

Cucina, a restaurant owned by Chef Gianni Scappin and Lois Freedman, debuted in 2006 and is housed in a sprawling farmhouse in the picturesque city of Woodstock, New York.

Seasonal and regional products provide the foundation of modern Italian fare.

Food prepared by Chef Scappin is straightforward and elegant, and he has subsequently introduced it to two more restaurants in the Hudson Valley.

Cucina exudes warmth in a rustic-chic environment with contemporary accents.

You may eat in privacy or with companions at one of the dining rooms’ 24 private tables.

Enjoy the sun on the spacious wraparound porch on bright days, or curl up by the fireplace on chilly evenings.

The Barn, a renovated 19th-century barn ideal for private gatherings, weddings, and festivities, is situated next to the restaurant.

Unwind at the Woodstock Inn on the Millstream

Serenity at the Woodstock Inn on the Millstream come together to make the ideal weekend retreat.

In addition to the property’s tumbling Millstream and luscious landscapes, the comfy, well-appointed rooms are rejuvenating for visitors of all ages.

The Millstream cascades down 1,000 feet of the stony riverbed, dashing from pool to pool, serving as the bed & breakfast’s focal point.

All of the amenities at the inn are of the best quality, including the luxurious Aveda toiletries, clean linens, and soft beach towels for swimming.

Visit the photo gallery for an overview of some of the natural splendor you’ll see while onsite.

The distinctive inn is the perfect destination if your travel goals involve seeing the arts, going on adventurous expeditions, or just relaxing and enjoying the surrounding natural beauty.

Explore Thorn Preserve

Thorn Preserve is made up of 60 magnificent acres close to the city of Woodstock in Ulster County.

The area is home to Overlook Mountain’s most beautifully painted views.

The vast grassland ecosystem, riparian woodland, and ponds make this region incredibly tranquil and restful.

From John Joy Road, manicured walking trails are easily accessible.

Additionally, it serves as the location of the Save the Hemlocks project, a Catskill Regional Invasive Species Partnership initiative.

Thorn Preserve remains untouched, enabling them to provide environmentally friendly education, sustainable farming, excellent stream management, and the perfect artists’ getaway.

Other Things to Do Nearby

Have a Relaxing Time at the Ashokan Reservoir

Sunny day at Ashokan Reservoir

Joseph Sohm /

Bagging the title of the top tourist spot in Woodstock, the Ashokan Reservoir deserves appreciation.

Simply watching the water flow here already feels therapeutic.

It is said that New York has the cleanest drinking water and flows from this very reservoir.

Colorful sunset reflecting on Ashokan Reservoir

Reid Dalland /

The lucent water that flows in this channel is unadulterated and suitable for drinking.

You cannot swim or do some water activities here, but you can still walk around the pavements and experience the peacefulness of the place.

Trees surrounding Ashokan Reservoir

Reid Dalland /

Take in Scenic Views from Overlook Mountain

Daytime view from Overlook Mountain

Danita Delimont /

Nature is breathtaking and unexpected, and this mountain is a testament to that.

You may take up a trail to explore Overlook Mountain from every angle and enjoy the road simultaneously.

The road is rocky, so it might take more time to reach the top.

Scenic view from Overlook Mountain

Mister.ev, CC BY-SA 4.0, via Wikimedia Commons

But once you do, you’ll feel everything was worth it.

You’ll witness even more breathtaking views as you get higher and higher.

Once you reach the uphill, take a deep breath—because you won’t even feel like blinking once you open your eyes!

South face of Overlook Mountain from Woodstock

True Pagan Warrior, CC BY-SA 3.0, via Wikimedia Commons

Hike Up the Shawangunk Mountains

Beautiful view from Shawangunk Mountains

Joey Scelza /

Shawangunk Mountains be one of your favorite places in Woodstock.

The hike up to the waterfall is easy and smooth.

The trail is a bit long, but it is worth a shot.

If you are looking for a dose of nature’s beauty, this is your spot.

Away from the commotion of the town, this place offers the utmost solitude.

A woman standing on a cliff of Shawangunk Mountains

Colin D. Young /

It gets even more beautiful as you climb your way up.

As it is said, the higher the hike, the better the view.

Nature untouched by human hands is always a delight to watch.

Spare an evening and spend time here.

It will be worth your time.

Fall-colored trees of Shawangunk Mountains

Colin D. Young /

Retreat to Onteora Lake

The waters of Onteora Lake

Mad Hare Imagery /

Nature beckons—heed its call and head to Onteora Lake.

It is very near to the town of Woodstock.

You should visit this spot to experience the tranquil atmosphere.

You can take a trail around the lake and identify a diverse range of flowers.

The trail is smooth and easy.

The lake is an attraction in itself.

Water flows in clear streams, and birds fly above.

The lake is surrounded by woods which makes it altogether more beautiful.

You will find yourself at peace here.

Admire the Opus 40

Landscape of Opus 40

Manuela Michailescu, CC BY-SA 4.0, via Wikimedia Commons

Opus 40 is a magnificent creation of art, curated over 37 years.

It was sculpted by a pioneer artist and represented the Aztec way of life.

It is unlike any other sculpture you’ll ever see.

View of the Opus 40

Dennis W Donohue /

Reaching the structure is a maze, so you must map your way out.

En route, many spots will make you pause your trek and gawk at them.

It would be best if you visited it in the evening when the atmosphere is more pleasant.

It’s s one of Woodstock’s hidden and less explored art pieces.

To understand and respect art in every form, you must visit Opus 40.

The top half of Opus 40

Dennis W Donohue /

Tour the Elena Zang Gallery

Elena Zang Gallery is one of the unique galleries in New York.

The gallery exhibits the work of nearly every renowned artist from New York.

It is an aesthetic spot to visit.

The venue is well-maintained, and the art pieces are gracefully showcased.

The collection is diverse and intriguing to see.

The gallery place is serene and peaceful.

You can spend an hour or two exploring and admiring the art.

The garden attached to the gallery is a good relaxation spot, too.

After touring the gallery, you can relax and stretch out in the garden area.

Also, you’ll find the best contemporary art pieces here.

You can buy some of them if they allure you enough.

The owner’s taste is impeccable.

Only the finest and most enigmatic pieces are displayed here.

Final Thoughts

Woodstock isn’t only notable for its summer musical theater season.

A little-known fact is that there are about 6,000 people that live in this town— and they include artists, religionists, and theater enthusiasts worthy of a lot of attention from across the country.

Consider Woodstock your next getaway destination, and use this list to navigate your way around the town.

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