Fun Things to Do in Woodstock – A Guide for Explorers and Adventurers

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Welcome to Woodstock – your perfect vacation destination! There’s something for everyone here, from its breathtaking mountains to the charming atmosphere.

Whether you’re a history buff seeking to uncover the town’s unique stories or an outdoors enthusiast itching for adventure, the possibilities are endless.

Woodstock, New York, is a cute little town in northern New York’s Ulster County. Technically, Woodstock is in the Catskill Mountains and is inside Catskill Park.

Best things to do in Woodstock

Enjoy unparalleled outdoor activities, savor delicious local restaurants and shops, and make memories that will last a lifetime. We now explore the many things to do in Woodstock. So what are you waiting for? Grab your map and pack your bags; it’s time to explore all Woodstock offers!

SHOP ON TINKER STREET

This is one of the best things to do in Woodstock. Shopping on Tinker Street in Woodstock, NY, is an absolute must-do! Boasting friendly mom-and-pop shops, the area is filled with vintage treasures, one-of-a-kind gifts, and novel pieces you won’t find anywhere else. Consider renting a bike from Overlook Bicycles to make it easier to explore.

As you go east on Tinker Street, check out Birchtree, Timbuktu, Shop Little House, Modern Mythology, Marigold Home of Woodstock, and Maverick Road. Don’t forget to swing by Three Turtle Doves or Rock City Vintage for some one-of-a-kind antiquated wear and Lily’s Boutique for the hottest hidden fits.

Finally, don’t miss out on Pegasus Footwear and Sparkle for shoes, accessories and knick-knacks. With so much to do and see it’s no wonder why Tinker Street Shopping is one of the best activities to do in Woodstock!

Things to Do in Woodstock

ENJOY THE FOODIE SCENE

The next time you’re in the beautiful woods of Woodstock, be sure to treat yourself to some of the area’s best dining establishments. We were excited to check out Yum Yum Noodle Bar and its customizable flavor combinations. These are the most important things to do in Woodstock.

Those delicious noodle bowls are worth a visit! Next up was Station Bar & Curio which offered us a unique experience – originally from Brown’s Station, this place is now a staple for crafty cocktails and mouth-watering brews.

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Just a hop away on Tinker Street, we found our way to Tinker Taco Lab, which served the freshest tacos topped with amazing flavors. And if you have any room left, snag sweets from Peace, Love, & Cupcakes! You won’t regret it. When in Woodstock, make sure to enjoy all these incredible food spots.

KARMA TRYANA DHARMACHAKRA MONASTERY

Experience the spiritual serenity of Karma Tryana Dharmachakra (KTD), located in Woodstock – the North American home to His Holiness the 17th Gyalwang Karmapa. This is also one of the best things to do in Woodstock.

Here, you can take in the majestic beauty surrounding you and bask in the restorative power of a meditative weekend lesson. Invite peace into your life with a traditional monastery tour, and then share some tashi delek – “goodness and happiness” – with your fellow visitors. Before leaving, check their website for upcoming events, so you don’t miss out on exciting opportunities.

Once you’re finished at KTD, head to the Overlook Mountain ruins, where Mother Nature will inspire a sense of tranquility.

There’s no better spot to find respite than this picturesque part of the Catskills, making it one of the top places to visit if you ever visit Woodstock!

OVERLOOK MOUNTAIN

Grab your hiking boots and hit up one of the most popular outdoor activities in Woodstock, NY: conquering the Overlook Mountain Trail! This 4.6-mile round-trip journey is moderate difficulty and takes around 3 hours to complete. If you’re feeling extra adventurous, include a visit to nearby Echo Lake for a 9.3-mile experience.

The main trailhead, which is directly across from Karma Tryana Dharmachakra, offers free parking, but keep in mind that spots fill up quickly on summer weekends. As you ascend on the old carriage road, enjoy the steady climb and take note of any Timber Rattlesnakes that may be lurking in the area – they’re known to frequent these trails.

Reaching the peak is worth it! You’ll be rewarded with spectacular views of the Hudson Valley, an impressive fire tower, and the ruins of the former Overlook Mountain Hotel.

Before heading back down, take in the stunning panorama, and don’t forget to snap some pictures! Though mountain biking, snowshoeing, and, of course, hiking are all welcome, please note that horseback riding and snowmobiling are not allowed.

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WOODSTOCK MUSIC FESTIVAL SITE

Made famous by the legendary 1969 Woodstock Music Festival, this town still carries an air of uniqueness and wildness that can’t be found anywhere else. This festival brought together over 450,000 people and top performers who preached peace and unity through music.

Though it was originally located 46 miles away in Bethel, New York, one can still enjoy its presence in Woodstock today! Take the brand-new augmented reality tour to see the festival grounds as they were in 1969, down to the stage’s model and the crowd’s energy. All thanks to a rented iPad!

Be sure to visit the Woodstock Museum at Bethel Woods Center for the Arts for an even more thrilling experience. With discounted tickets available on their official website, you can discover the stories and legends of this iconic 1960s gathering. It’s truly a generation-defining moment.

Things to Do in Woodstock

OPUS 40

This seven-acre environmental masterpiece was carefully crafted with bluestone quarried by pioneering artist and professor Harvey Fite from the surrounding area. Spanning almost four decades in the making, this Registered Historic Place is truly breathtaking.

The delightful blend of ancient Mayan and Aztec stonework with its natural surroundings gives Opus 40 an enchanting atmosphere. With dry-stone ramps, pedestals and platforms creating a captivating scene, one can only imagine all this site offers.

Tickets can be purchased online for a springtime visit to soak up all the beauty this sculpture offers.

Final words

These are the things to do in Woodstock. Make your way to Woodstock and experience this town’s unique offerings! From thrilling outdoor activities to captivating culture and history, there’s something for everyone in this vibrant destination.

Go on an invigorating hike amidst miles of trails, explore the fascinating streets downtown, or take a relaxing stroll – whatever you choose will be an outstanding experience.

There’s no shortage of attractions, activities, and eateries to make your stay even more enjoyable. It’s time to see what Woodstock has in store – come and make memories that will last a lifetime.

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