Top Picks

Hotel Kinsley Restaurant

(Kingston, 25 minutes)

Another phenomenal option with food quality and taste similar to Silvia, though perhaps a bit more meat-centric, don’t be fooled though, lots of veggie options, too! Great pasta additions as well and their vegetable curry is to die for.

We would suggest taking a look at their wine-by-the-bottle list, which is extensive and includes some excellent NY-produced favorites and have one of their handcrafted cocktails to complete your experience.

(845) 768-3621


(Woodstock, 10 minutes)

Top pick for a sexy and vibrant ambience combined with delicious food selection. You’ll feel like you’re right back in NYC. Silvia has a sustainable evening dining menu featuring locally-sourced and thoughtfully-curated meats, vegetables, and an incredibly unique cocktail menu and vibrant bar atmosphere.

SILVIA reflects our vision of connecting food and people with back to basic cooking that is honest and sustainable. Our open kitchen with a wood fired grill and organic vegetable-centric pantry, reflect our commitment to locally sourced ingredients.

(845) 679-4242


(Woodstock, 10 minutes)

The contemporary Italian menu is based on seasonal and local ingredients. Cucina radiates a warm atmosphere in a country chic setting with modern touches. Dine with friends at the 24-seat communal table or more privately in a dining room. On warm days, bask in the sunlight on the large wraparound porch or settle in by the fireplace on winter nights.

(845) 697-9800

Deer Mountain Inn

(Tannersville, 40 minutes)

In addition to their regular dining menu that switches it up on an occasional rotation, we highly recommend their tasting menu (Call for details / reservations and seating times as they often change). Not for vegetarians or those who prefer to curate their own plates / make specifications, but if you’re open for doubling-down on adventure after that arduous, thrilling hike, this tasting menu is a decadent addition to your upstate experience! The decor and vibe of this space is incredibly true to the Catskills in every way possible. Nothing is placed here without obvious yet effortlessly-communicated thought.

(518) 589-6268

Bread Alone

(Boiceville, 5 minutes)

A daytime cafe and coffee shop open 9-5pm right down the road from us! Serving organic, fresh baked bread and pastries of all varieties made each morning in their bakery. Offering both plant-based and traditional fare options and amazing soups each day. All food has very high quality ingredients! An Ashton Hills staple! (845) 657-6057

Phoenicia Diner

(Mt. Tremper, 10 minutes)

People literally come upstate just to eat here! Maybe you’ve seen their merchandise and trucker hats appearing all around Brooklyn. Phoenicia Diner is a truly iconic upstate destination, you MUST have breakfast here at least once during your stay. Other than Bread Alone, it is essentially the next closest place to our house! Lucky you!

(845) 688-9957

Brunette Wine Bar

(Kingston, 25 minutes)

Nothing but the best natty-wine curations here! You’ll find some on-trend favorites, but also some hidden gems, too. Think you can’t find orange wine in the Catskills? They’ve got a beautiful selection here. Tapas / small plates, too. The Trout Roe Nachos are actually to die for.

(845) 802-0837

Lis Bar

(Kingston, 25 minutes)

The cocktail program here is playful, sophisticated, and generally spirit-forward. This is the sort of place where we’d want to find a designated driver to take us home because choosing just one cocktail feels more sinful than trying them all! Okay, maybe not all if we’re thinking of our guts and morning hangovers but yeah, them ALL! Their polish-centric tapas and small plates are also a perfect union of tradition and innovation.

(845) 514-2350