15 Best Things to Do in Woodstock, NY

15 Best Things to Do in Woodstock, NY

New York has its own charm when it comes to tourism and lifestyle. It remarkably stands apart from the rest of the States. But also know that New York is diverse in itself.

There are innumerable towns and cities composed in it. All of them are unique and culturally active in their own sense. They are not interlinked, all of them stand as a separate entity.

One such town is Woodstock. It is more of a village and township. The town is an art devotee. It is a low-key town with a lot of captivating things to do. It has everything you ever imagined for.

You are in for a joy ride! So, what’s the wait for? Let’s board the train around Woodstock and look out for bewildering things to do.

Exhilarate at Ashokan Reservoir

Ashokan Reservoir
Joseph Sohm / Shutterstock.com


Bagging the title of the top tourist spot in Woodstock, Ashokan reservoir deserves appreciation. In this hustle-bustle of the city, do you crave minutes of silence and solitude?

According to us, even watching the water flow is therapeutic. It is researched that Newyork has the cleanest drinking water and that flows from this reservoir.

The lucent water that flows in this channel is unadulterated and suitable for drinking. You cannot swim or do some water activities here, you can still walk around the pavements and experience the peacefulness of the place.

It is the best place to start off your expedition around Woodstock. Refresh your mind and soul first and then start soaking the Woodstock lifestyle.

Take a Stroll on The Tinker Street

Tinker Street in Woodstock
Beyond My Ken, CC BY-SA 4.0, via Wikimedia Commons


Now that you are fresh and invigorated with energy and positive vibes, head over to Tinker Street. This spot is for the shopping buff in you. It is the most enjoyable and lively place to walk and shop simultaneously.

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

There are art pieces displayed on the walls too, creating picturesque spots to snap a picture or two. You can catch hold of some vintage postcards, personalized apparel, and customized jewelry to take back home.

Do negotiate for prices, if the situation may occur. The products are affordable but just in case. You’ll enjoy your time here, we guarantee you that.

Admire the Massive Opus 40

Opus 40
Manuela Michailescu, CC BY-SA 4.0, via Wikimedia Commons


Woodstock is synonymous with art and Opus 40 is a testament to the fact. It is a magnificent creation of art, curated over 37 years.

It was sculpted by a pioneer artist. It represents the Aztec way of life. It is unlike any other sculpture you’d ever have seen. Reaching the structure is a maze, you need to map your way out.

En route, many spots would pause your trek and would make you gawk at them. You must visit it in the evening, as the area is open.

Evenings would be better because of the pleasant atmosphere. Note that is one of the hidden and less explored art pieces. If you understand and respect art in every form, then you must visit Opus 40.

Hike to The Shawangunk Mountains

Shawangunk Mountains
Joey Scelza / Shutterstock.com


Nature's marvel again! Shawangunk Mountains will happen to be your best destination ever. The hike up to the waterfall is easy and smooth. The trail is a bit long but is worth giving 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 has nothing but solitude to offer. It gets even more beautiful as you climb your way up.

As it is always 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.

Pray at The Holy Transfiguration Church

Holy Transfiguration Church
Dmadeo, CC BY-SA 3.0, via Wikimedia Commons


It is a modestly beautiful church. This tiny church holds a massive religious significance. Located in between the woods, it is an aesthetically looking edifice.

Decorated with the infamous stained glass windows, this church is beautiful. This is more of an offbeat location as it is not visited much. But it deserves a lot more recognition.

The church is always open for devotees. There is a baptism pool attached to the shrine too. It is a little old church with intriguing details. The architecture is old and Victorian. A rustic spot to pray for the world's well-being and happiness.

Catch a Show at Bearsville Theatre


Bearsville is a renowned theatre in Woodstock. Every person who visits this place is astounded and 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.

The staff is super friendly and really understanding. They suggest the perfect shows and seats for you. You can catch an afternoon. Keep your eyes open for some new show or gig. It will be a fun and worthwhile experience here.


One of the most unique galleries in Woodstock is Elena’s. The gallery is composed of works of every renowned artist from Newyork. 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 watch. The gallery place is serene and peaceful.

You can spend 1-2 hours here to explore and admire 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 if it allures you enough. The owner’s taste is impeccable. Only the finest and mystifying pieces are displayed here. Do not miss out on this gallery, please.  It will be worth it, trust our recommendations.

Touch of Music at Woodstock Playhouse

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 accurate place to understand and get to know Woodstock Music. There is a plethora of musical drama and theatre plays happening in the Playhouse.

Located right on the main road, it is easy to find. The sitting is totally 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 onstage energy of artists is contagious. The audience gets filled with zeal and happiness too. You’ll feel you are on Broadway, even though you’d be sitting in Woodstock. That’s the kind of enthusiasm and stage show this theatre holds. Fasten your belt! You’re up for a ride.

Overlook the ‘overlook Mountain’

Overlook Mountain
Danita Delimont / Shutterstock.com


No, it isn’t a riddle. You read it right. The mountains are named ‘Overlook’. Nature is truly beautiful and unexpected.

This mountain stands as a testament to that fact. You may take up a trail to explore the mountain from every angle and enjoy the road simultaneously.

The road is rocky so it might take more time to reach the place. But once you do, you’ll feel everything was worth it. As you’ll reach higher and higher you’ll witness a breathtaking view.

The gravels on the path shouldn’t stop you. Once you reach the uphill, take a deep breath. Because once you’ll open your eyes you won’t even feel like blinking.

Attain Solitude at Karma Triyana Dharmachakra

Karma Triyana Dharmachakra
Michael Pawluk / Shutterstock.com


Karma Triyana Dharmachakra is a Tibetan monastery located in Woodstock. It is open for everyone, not just limited to Buddhists. The monastery serves as a retreat center.

If you are looking for a peaceful escape out of the city then this is your spot. The spirituality of this place is pure and composed.

You can meditate or just gather your thoughts by taking deep breaths. The atmosphere is charged and calms your mind instantly. Regardless of what you believe in or worship, you should visit this place.

It will help your mind to be steady and slow. Also, knowing a new culture is never bad. It will in turn increase your knowledge and promote diverse thinking.

Mower’s Saturday Market Visit


Flea markets are always fun and vivid. Mower’s is no different from that. The market is open on weekends only.

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’d get a lot of varieties to try and select.

You need to browse through a lot of stalls and vendors to find suitable items for you. Snacks are available too if you feel hungry in between your shopping spree. The vendors are really friendly and they do negotiate with the prices.

You don’t need to spend a lot of time here, you can give a quick glance and get your desired things. Be sure of your choices and you will definitely get your hands on the best of best. Go shopping in the morning though. It would be calmer, less crowded, and clumsy.

Delectable Bites at Bread Alone


Craving a sweet tooth or bread? You are in for a treat then. Bread Alone serves fresh and scrumptious bakery items. They have assorted pastries, gooey cupcakes, crispy croissants, and not too soft cookies. They are open for foodies from 7 AM to 5 PM. You can visit anytime and fulfill your cravings.

Also, hey coffee addict, hang on we have something in store for you too. Bread Alone brews dark and creamy coffee.

They add the perfect amount of sugar and tops it with whisked cream. In addition, you can buy a cookie. It would enhance the taste and feel of the coffee.

Listen to Live Music, Anywhere

Drum circle gathering in Woodstock
littlenySTOCK / Shutterstock.com


Quite literally, you can listen to live music anywhere. Woodstock’s soul is etched to music and is evident from the vibe you get there. Every corner has someone or the other playing an instrument or humming a tune.

You should venture out in the streets at night. Because many people would be strumming some amazing tracks on the road. The atmosphere is lively.

After some time you’ll find yourself jamming to their beats and maybe shake a leg or two. You will thoroughly enjoy the night. And after some days, you’ll be found humming those tunes you heard back in Woodstock.

Stop by At the Sun Frost Farms


If you are looking for farm-fresh products, Sunfrost 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 for. Also, there’s an eatery too which serves juices and salads.

Organic items should be your priority always and it is Sunfrost Farms’ too. So, visit it early in the morning and start your day with vital and correct vitamins.

Retreat at Onteora Lake

Onteora Lake
Mad Hare Imagery / Shutterstock.com


Nature’s calling you, understand the signs, 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. Spend an evening here.

Pack your picnic basket and sheets and lay down there for an infinite time. The lake is surrounded by woods which makes it altogether more beautiful. You will find yourself at peace here.

Woodstock was indeed beautiful, wasn’t it? It consists of everything you ever wished for in your dream destination.

We never wanted to get off this train, but here we are back at our station. So, let’s move out and plan our next trip as soon as possible. Woodstock, until next time!