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What to Do, Eat, and See During a Day Trip to Woodstock

The Mower’s Market in Woodstock. Photo by Sabrina Sucato

The iconic upstate town is a hub for farm-fresh food, community shopping, and, of course, entertainment in the Hudson Valley.

By Sabrina Sucato, with additional reporting by Rebekah Hendricks

In the world of music, Woodstock is legendary. The modest Hudson Valley town unwittingly became a creative landmark in 1969 when the Woodstock Music Festival took the region by storm. Although the fest itself went down in nearby Bethel, Woodstock earned the title spot thanks to its local reputation as an artistic haven.

Nowadays, the famous town continues to attract innovators of all sorts. Crafters sell their wares while foodies whip up delectable eats and musicians jam out. With so much going on in one zip code, Woodstock is a day tripper’s paradise.

9 a.m. – Enjoy an egg-cellent meal at Oriole 9

17 Tinker Street, Woodstock

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At Oriole 9, breakfast is the most important meal of the day. That’s why the eatery offers the morning menu at all hours. If you love eggs, go for the goat cheese omelet filled with delicious baby spinach and goat cheese, served with crisp toast and your choice of a fresh salad or potatoes.

10:30 a.m. – Hike your way up Overlook Mountain

Parking on Meads Mountain Road, Woodstock

On a sunny day, venture on over to Overlook Mountain for a challenging hike that rewards you with one of the most picturesque views in all of the Hudson Valley. Although the full hike takes about three hours, feel free to go at your own pace; the view from the top of the Overlook Fire Tower makes the trek worthwhile. The trail is great for dogs and kids, making it an ideal option for families. As you approach the top, make a detour to the abandoned hotel for a few creepy but beautiful photos. Be forewarned—parking is a challenge since the designated lot only holds 20 or so cars.

2 p.m. – Rave about ramen at Yum Yum Noodle Bar

4 Rock City Road, Woodstock

With locations in Kingston, Red Hook, and Woodstock, Yum Yum is a Hudson Valley staple. Take advantage of the noodle bar options by customizing your bowl with different noodles, broths, and protein options. With vegan and gluten-free dishes scattered throughout the menu, this ramen joint is perfect for anyone with dietary restrictions.

Related: Radio Woodstock Celebrates Local Sounds on 100.1 WDST

3:30 p.m. – Go gallery hopping in Woodstock

Tinker Street, Woodstock


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With its rich creative history, it’s no surprise that Woodstock is home to art galleries galore. Spend an hour or two hopping from one art space to the next, taking in everything from photography and sculpture to ceramics, contemporary art, and more. If you visit with family or friends, make a game out of it as you pick and choose your favorite works in each space.

5 p.m. – Shop till you drop on Woodstock’s Tinker Street

Tinker Street, Woodstock


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All roads in Woodstock may not lead to Tinker Street, but they should. Woodstock’s main drag is a must-visit during any trip into town, simply because it provides such a strong snapshot into community life. Stop into any of the clothing, home goods, and jewelry stores that line the road to pick up one-of-a-kind gifts and goodies. If you happen to spot something for yourself, snag it while you still can—many of the goods for sale in Woodstock are artisan originals. Essential stops include The Golden Notebook for excellent reads, Candlestock for a range of handmade candles, and Woodstock Music Shop for instruments and vinyl.

7:30 p.m. – Eat farm-to-table Italian at Cucina

109 Mill Hill Road, Woodstock

salad at cucina in woodstock

A salad at Cucina. Photo by Sabrina Sucato

If you plan your day trip in advance, do yourself a favor and call in a reservation to Cucina, Woodstock’s fan-favorite Italian restaurant hidden inside a farmhouse. Savor Mediterranean classics like stracciatella soup, burrata salad, and thin, crusty pizzas served hot from the oven. If you don’t have room for dessert, don’t be surprised. The food is just that good.

8 p.m. – Jam out at the Colony

22 Rock City Road, Woodstock

What’s Woodstock without live music? The Colony’s cozy, historic hotel interior and expert sound engineering provide guests with an intimate musical experience. All of that dancing will take a lot out of you, so be sure to refuel with beverages and bites like a burger dressed with iceberg lettuce, red onion, pickles, American cheese, and the mouth-watering Colony secret sauce neatly sandwiched between soft potato buns.

9:30 p.m. – Spend the night at Woodstock Way Hotel

10 Waterfall Way, Woodstock

After all the excitement of a day trip in Woodstock, it only makes sense to wind down the evening in town. Book a room at Woodstock Way Hotel, a contemporary retreat that’s tucked behind a waterfall next to a babbling brook. The hotel embraces a natural aesthetic and welcoming vibes, with unique furnishings and eye-catching art strewn throughout. For larger parties or extended stays, Woodstock Way boasts a number of residences as well.

Related: Mohonk Mountain House Named a Top Family Destination

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