Weekend in Woodstock :: A Guide To America’s Most Famous Small Town

Weekend in Woodstock :: A Guide To America’s Most Famous Small Town

The first thing you should know about Woodstock is that it is not where the 1969 Woodstock Festival took place. That happened about 90 minutes away in Bethel Woods. But music history buffs and hippies at heart will still love this destination in New York’s Hudson Valley, which has everything you could want in a weekend getaway: nature to explore, delicious restaurants to eat at, cute shops and plenty of local quirks.

A Weekend in Woodstock, New York

Take a walk around town and you’re sure to spy locals strolling in and out of organic cafes and art galleries in tie-dye garb or standing in the town’s center holding signs that protest the war. In stark contrast, you’ll also find upscale, gourmet restaurants and contemporary shops that lure Manhattanites craving a break from New York City’s crowds.

Weekend in Woodstock, New York

Weekend in Woodstock, New York

Weekend in Woodstock, New York

Weekend in Woodstock, New York

Woodstock has been an artists’ colony since the early 1900s, long before the namesake festival. The Arts and Crafts Movement found a home there in 1902, when the Byrdcliffe Colony (which is still around today) was founded. When a school for artists opened a couple of years later, the town’s future as a haven for artists, musicians and creative thinkers was set. Since then, Woodstock has been home to famous musicians like Bob Dylan and Levon Helm of The Band.

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Weekend in Woodstock, New York

Weekend in Woodstock, New York

So what’s there to do in America’s most famous small town? Quite a bit! On a chilly fall weekend in mid-November, I made a reservation at the hippie-chic Hotel Dylan ($189 nightly rate) after stumbling across irresistible photos of the property on Instagram, and the rest of my plans fell into place.

First things first, let’s talk about food. My favorite kinds of trips are the ones where you wander from eating establishment to eating establishment, maybe stopping to check something out along the way. A weekend in Woodstock was the perfect opportunity to do just that, with a plethora of gourmet and farm-to-table restaurants located in the area. New York City might be known as a foodie destination, but the food in the Catskills region just tastes better. That’s because it’s as fresh as can be, grown on the farm down the street or sometimes even in the restauranteur’s backyard.

Here are some of the best places to eat in Woodstock:

Oriole 9 –  Oriole 9 co-owner Nina Paturel’s parents ran a place called Café Espresso in the 1960s, where artists like Bob Dylan and Joan Baez were known to hang out and make music on lazy summer days. Hoping to continue the family business, she opened her own restaurant with husband Pierre-Luc Moeys, who happens to be a French and classic Italian-trained chef. The cafe, open daily for brunch and lunch, focuses on globally-inspired dishes and locally-sourced ingredients. They have also partnered with a local school to share their dedication to sustainable living with the next generation. Kids learn about agriculture and grow organic food for the restaurant on campus. Check out the menu for daily, farm fresh specials and when all else fails, go for the Cuban sandwich.

Brunch at Oriole 9 in Woodstock, NY

Brunch at Oriole 9 in Woodstock, NY

Phoenicia Diner – Not technically in Woodstock, the Phoenicia Diner is about a 20 minute drive away that’s worth every minute on the road. One of the more affordable eateries in the area, the diner looks like an old-school roadside stop yet on the inside, focuses on modern comfort food that’s local, fresh and loosely healthy (as in, whole wheat pancakes). Since it was Hudson Valley Cider Week during my visit, I had to go with the Apple Cider Pancakes. But I also tasted the restaurant’s bacon, which was YUM, and huevos rancheros (also quite good).

Weekend in Woodstock, New York

Weekend in Woodstock, New York

Weekend in Woodstock, New York

Red Onion – Located just east of Woodstock in Saugerties, the Red Onion was our first meal of the weekend. Although it closed at ten, the restaurant welcomed us with open arms at 9:15 and didn’t rush us out at all. From the outside it looks like a private home, and on the inside you’ll feel as though you’re part of a cozy dinner party. While prices are comparable to Manhattan, the food is extremely delicious. If you’re trying to be healthy, go for Chopped Salad with Chicken, which was probably the most satisfying salad I’ve ever had in my life. If you prefer to splurge, stick to the steak frites. The peppercorn butter on top is mouthwatering, and to slightly offset its fattening effects you can always swap the frites for a vegetable side.

Weekend in Woodstock, New York

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Weekend in Woodstock, New York

Rick’s Wood Fired – Maybe it was because I’d had an extra glass of wine, but this pizza was seriously some of the best I’ve ever had. Could New York’s best pie be from outside NYC? Located next to indie theater Upstate Films, Rick’s Wood Fired is also inside a house, which provides for an intimate atmosphere as you wait for your pizza to exit the authentic wood fired oven. If you do go here, don’t miss the chance to try their homemade mozzarella appetizer. It’s worth every calorie and dairy stomach ache.

Pizza at Rick's Wood Fired in Woodstock, New York

Mozzarella at Rick's Woodfired in Woodstock, New York

Sunfrost Farms – Proving that sometimes the best part of traveling is getting lost, we stumbled across this super market slash juice bar & cafe after a wrong turn. The store is the leading retailer of local and organic farmers, and NYC dwellers can pick up some truly fresh produce before heading back to the city where the checkout line at Whole Foods takes an hour. After a three hour hike in the cold, we were freezing and beyond happy to warm up at Sunfrost Farm’s counter with an order of homemade chicken noodle soup and hot chocolate.

Sunfrost Farms in Woodstock, NY

Sunfrost Farms in Woodstock, NY

After you’ve sufficiently stuffed your face, you can burn it off with a hike to the top of Overlook Mountain. The trail begins across the street from a Tibetan monastery (yes, you read that correctly), so you can’t miss it even if your GPS is wonky. It’s about three hours round trip and hard if you’re not a regular practicioner of cardio. The trail itself is relatively clear and easy, but it is a moderately steep, nonstop uphill climb until you reach a fire tower at the top. When you’re almost there, you’ll see the ruins of an old hotel and many silly people wandering around inside them even though signs outside clearly state that it’s not safe. What is safe is climbing the fire tower on top of Overlook Mountain for stunning views of the Catskills and surrounding Hudson Valley region. Just hold on to the railings as you ascend!

A Weekend in Woodstock, New York

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Abandoned hotel on Mount Overlook in Woodstock, New York

Weekend in Woodstock, New York

Hiking in Woodstock, New York

View from the top of Mount Overlook in Woodstock, New York

Weekend in Woodstock, New York

There is another nearby hike that is much shorter and very popular, and it will take you to Kaaterskill Falls. I hoped to do this one as well, but on our second day of the weekend in Woodstock, temperatures were pretty frigid and we didn’t feel like spending too much time outdoors. So instead we went… shopping!

Woodstock is known for its art galleries and antique stores, but since I personally choose to spend all my dollars on fashion and flights, I popped into a few clothing stores instead. The two I’d recommend: Sorella of Woodstock, which stocks some great women’s clothing and accessories (I snagged a blanket-like sweater to stay warm for $69), and Woodstock General Supply, a men’s and women’s boutique that I can only describe as outdoorsy-meets-chic. I also spotted quite a few handwoven rugs that I instantly recognized from the souks of Morocco… turns out the owner is Moroccan!

Weekend in Woodstock, New York

Sorella of Woodstock

Pictured: Sorella of Woodstock

If you get chilly during your visit to Woodstock’s center, stop into colorful Taco Juan’s for Mexican hot chocolate. Likewise, if you’re there in the summer, you can hit up the same place for the town’s best ice cream.

A Weekend in Woodstock, New York

A weekend in Woodstock was the perfect short escape that combined adventure and relaxation away from the crowds of New York City. I’m hoping to go back in the summer, when I can explore more of the region’s hiking trials and swimming holes, and of course, to try the ice cream.

A Weekend in Woodstock, New York

Weekend Road Trip to Woodstock, New York

If you’re planning a visit to Woodstock, I recommend driving as there are no train stations nearby and limited public transportation options within the town. The closest train stations are Poughkeepsie (Metro North) and Rhinecliff (Amtrak). There is a bus that goes directly from NYC to Woodstock, but if you choose that route you won’t have much freedom when you arrive.

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