6 of the Best Woodstock Restaurants And Cafes

Woodstock isn’t a hidden gem.

Artists and musicians have been flocking to the Catskills town for decades. More recently, New York City hipsters have joined the fray in their quest to escape Brooklyn and Manhattan even if only for a few days.

Some of these city folk come to experience culture at Woodstock hot spots like Levon Helm Studios and The Woodstock Playhouse or as part of a musical pilgrimage to the Big Pink house (which is actually in Saugerties but we digress). Others come to the area to soak up nature’s bounty on the nearby Ashokan Reservoir hiking trail as well as in Catskill Park and at the Opus 40 sculpture garden. And a few, like us, are all about the food.

Fun Fact
Woodstock (the city) achieved global fame in 1969 for a three-day concert featuring classic rock artists including Jimi Hendrix, Jefferson Airplane and Joan Baez. Ironically, the iconic concert actually took place on a farm in Bethel, more than a hour’s drive away from Woodstock. Learn more about Woodstock (the concert).

No longer a hippie hideaway, Woodstock has an established New York community that includes aging members of the counter culture generation plus a whole new crop of hipster residents. Many have opened independent shops that sell a mix of appealing vintage pieces and designer items on Tinker Street, while others have opened farm-to-table restaurants, brew pubs and cafes.

Despite its deceptively laid back atmosphere, Woodstock, like much of the Catskills, isn’t cheap. While its restaurants and cafes aren’t as pricy as Manhattan, they’re not far behind. We’re not suggesting that you should skip Woodstock. If you did, you’d be missing out on experiencing one of the Hudson Valley’s cutest towns.

Instead, the key is to spend your calories and money at the right spots. Read on to discover six places to start your eating journey in Woodstock.

Once we caught our first glimpse of the open fire grill at Silvia, an upscale Woodstock restaurant that opened in July of 2017, we knew that its chefs were serious about food. Ironically, we didn’t see the kitchen again until the end of our meal since we opted to dine outside on the restaurant’s expansive patio. But that doesnt mean that we didn’t taste the kitchen’s solid craftsmanship in the restaurant food.

More than a local favorite, Silvia is destination dining for food travelers due to a menu that pleases vegetarians, vegans and omnivores alike. The bistro’s globally-inspired menu features a variety of meat-free options as part of its commitment to sourcing local, seasonal and sustainable products.

While Silvia isn’t the most expensive restaurant we ate at in the Catskills, that dubious honor goes to the far more gastronomic DeBruce in Livingston Manor, it’s the opposite of cheap. Accordingly, we chose to share three plates – a grilled halloumi starter, spicy brussels sprouts topped with crispy shallots and a wood-smoked pork chop – to save both money and stomach space. Don’t worry. We each ordered our own local craft beer.

While the pork chop initially caught our eyes due to its bold inclusion of Vietnamese food elements, the brussels sprouts side turned out to be our favorite dish of the meal. Big in size and even bigger in spicy flavor, the flavorful morsels could almost entice us to give up meat. Almost.

Pro Tip
Silvia ‘politely declines’ substitution requests. Consider yourself warned.

Silvia is located at 42 Mill Hill Road, Woodstock, NY 12498, United States.

When we heard that the folks behind the Phoenicia Diner had opened a barbecue joint in Woodstock, the question wasn’t if we would eat at Dixon Road Side. Instead it was when the fateful act would happen.

As it turns out, we stumbled into the casual shed during a night of grazing. We were too late for the BBQ beef brisket plate which had sold out (oh no!) but just in time for a chopped brisket sandwich (hooray!) and a side of baked beans (yay!).

Once we got over the fact that we’d missed out on the brisket platter, we thoroughly enjoyed our messy but tasty chopped brisket sandwich which was flavored with paprika and masala and topped with onion rings. Even better, we were more than a little bit happy when we realized that our baked beans had both molasses and chunks of bacon in the mix.

This is a Catskills restaurant that sources products from local farms, “slaughters to order” and seasons meat with a simple but flavorful salt rub. It’s also a restaurant that fries chicken to golden crispiness.

Pro Tip
Don’t skip the peach hot sauce if you’re a condiment junkie. Not only does the sauce taste good, but it’s also a local Hudson Valley product.

Dixon Road Side is located at 261 Tinker Street, Woodstock, NY 12498, United States.

Important Update – Shindig Has Permanently Closed.

Food travelers without the budget for Silvia (see above) can enjoy a casual lunch at Shindig, a cheerful restaurant in the center of Woodstock. Open since 2014, Shindig’s comfort food menu features numerous burger options including turkey burgers, black bean and beet burgers and even Impossible burgers.

During our lunch, we ordered a Shindig Smash, a double patty sandwich with cheddar, onions, lettuce, pickles and a special sauce, opting for locally sourced grass-fed beef instead of the aforementioned protein options. We also chose fries over tater tots, sweet potato fries and salad. Since we live in Portugal, we crave the classic American sandwich combination and eat it whenever we travel in the United States.

Discover more classic American sandwiches.

Open for breakfast, lunch and dinner plus brunch on the weekend, Shindig gets its nightly party vibe from bartenders who craft inspired cocktails like blackberry soju lemonade and peach sangria behind the restaurant’s long bar. Eating at Shindig at noon, we skipped the cocktail menu and orders coffees instead.

Pro Tip
Grab a coffee to go at Shindig’s alley takeaway window.

Shindig was located at 1 Tinker Street, Woodstock, NY 12498, United States. It has permanently closed.

Thanks to Bread Alone Bakery, Woodstock locals and visitors can begin their day with a range of artisan breads as well as pastries including danishes, cinnamon buns and sticky rolls. Then, as the day continues, they can indulge in chicken salad sandwiches, soups and salads too.

Daniel Leader left NYC and opened his original Catskills bakery in Boiceville, just 10 miles from Woodstock, back in 1983. It wasn’t long before Leader, along with partner Sharon Burns-Leader, added bakeries in the Hudson Valley towns of Rhinebeck, Kingston and, of course, Woodstock.

After getting his original inspiration from Parisian patisseries in the early 80s, Leader started baking traditional sourdough boules with organic stoneground flour. The Catskills bakery has been using local products and ingredients before the practice was trendy.

That all being said, we were a little disappointed with our breakfast. The pretty pastries provided a serviceable start to our day but were lacking in tenderness. As for the bitter coffee, it was surprisingly ‘old school’ considering the bakery’s specialty coffee pricing.

Pro Tip
You can find Bread Alone’s bread beyond the Hudson Valley. The Catskills bakery distributes its bread to restaurants and specialty shops in NYC, Connecticut and New Jersey.

Bread Alone Bakery has multiple Catskills locations. We ate the bakery located at 22 Mill Hill Road, Woodstock, NY 12498, United States.

Important Update – Olsen and Company Has Closed Its Woodstock Location. However, its original Saugerties is a short drive from Woodstock

Olsen and Company may be relatively new in Woodstock, only open on Tinker Street since late 2020, but it’s far from a new Catskills cafe. The Olsen clan opened their original shop in Saugerties three years earlier.

Though we visited the Woodstock location specifically to satiate our specialty coffee habit, Olsen and Company doesn’t just brew coffee. The multi-generation business also serves lunch and stocks local products like maple syrup from Platte Creek Maple Farm and raw honey from Bee Hollow Farm on its shelves.

Taking local souring further, Olsen and Company gets key food items from businesses like Catskill’s Catskill Bread Co. and Saugerties’ Sow Good Bakery. Tasty treats are on display at the counter, a display that we couldn’t resist.

The shop also sells coffee mugs created by local Woodstock potter Brad Lail. We thought about buying a pair until we saw each mug’s $38 price tag. Ouch! Unlike the pastries, we were successful in resisting the mugs.

Pro Tip
Pre-order your purchase if you know you want to or if you’re in a rush.

Olsen & Company has closed its Woodstock location. The Saugerties cafe is located at 11 Jane Street, Saugerties, NY 12477, United States.

Technically in Shokan, a stone’s throw from Woodstock and right by the Ashokan Resevoir, Fruition Chocolate Works is a must stop for food travelers who visit Woodstock – especially those who appreciate bean to bar chocolate. It’s also a must stop for those who appreciate good coffee. We fit into both categories.

You may have heard of Fruition before. Owner Bryan Graham has received international recognition for his innovative Catskills chocolate operation. Graham sources beans from countries around the world and crafts small batches by hand. The resulting chocolate is magical.

While you can order Fruition colorfully wrapped chocolate bars and boxes of equally colorful caramels online, certain items are only available at the Shokan shop. We’re talking about ice cream sundaes, crafted drinks and hand-selected pantry items.

A highlight of visiting Fruition is drinking its tasty beverages. Options include Thai iced tea crafted with Thaiwala Tea from Portland and hot chocolate featuring Fruition’s sipping chocolate.

During our visit, we shared a bourbon caramel latte crafted with brown butter caramel and a shot of espresso sourced from Massachusetts-based Barrington Coffee Roasting Company. One sip of the bourbon caramel latte was a revelation. By the time we finished the decadent caffeinated cup, we wanted to return the next day for more.

Pro Tip
Drive to Fruition Chocolate Works and order a bourbon caramel latte. It’s one of the best coffee drinks in the Catskills.

Fruition Chocolate Works is located at 3091 NY-28, Shokan, NY 12481, United States.

You’d be foolish to stop at six eateries in Woodstock. Keeping in mind that each business is open on different days of the week, check the websites for the following additional spots and plan your Woodstock eating plan accordingly:

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