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

Wikimedia Commons / Niranjan Arminius

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

In the world of music, Woodstock is legendary. The modest upstate New York 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 city continues to attract innovators of all sorts. Crafters sell their wares while foodies whip up delectable eats and musicians strum their stuff. With so much going on in one zip code, Woodstock is a day tripper’s paradise.

Read on to see how to make the most of a day in town.

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

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 Poached Artichoke, stuffed with truffled scrambled eggs, or the Kale and Mushroom Bread Pudding Skillet, served with two eggs and mushroom gravy.

17 Tinker St, Woodstock

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

If the weather cooperates, 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 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 warned — parking is a challenge, since the designated lot only holds 20 or so cars.

 353 Meads Mountain Rd, Woodstock

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

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.

4 Rock City Rd, Woodstock

3:30 p.m. – Go gallery hopping

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 locale.


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5 p.m. – Shop ‘til you drop on Tinker Street

All roads in Woodstock may not lead to Tinker Street, but they should. The city’s main drive 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.

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

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.

109 Mill Hill Rd, Woodstock


Related: What to Eat and Where to Go in Saratoga Springs

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