Orange County is about an hour north of Manhattan, and has become many city-dwellers’ home away from home because of the sheer bounty of its attractions. Visitors flock to Orange County for the hiking and biking trails, art and cultural experiences, historic sites, farm-fresh bounty and bountiful shopping opportunities—but stay for the fun night life.
Much of the merrymaking is headquartered at the dozens of breweries, cideries, wineries and distilleries that call Orange County home. If you’re thirsty for local libations with a side of night life, read on—we have the scoop on after-hours entertainment.
Newburgh Brewing Co.
88 South Colden St., Newburgh, NY
Wednesday: 4-10 pm
Thursday: 4-11 pm
Friday: 4-10 pm (10% of total sales go to a local charity)
Saturday: 12-10 pm
Sunday: 12-6 pm
Since opening its doors in 2012, Newburgh has cranked out more than 120 styles of beer, ranging from traditional to funky. The roomy, light-filled taproom features communal seating and an array of board games, vintage video games, and cornhole.
Drinks: A range of constantly rotating seasonal housemade beers, plus local cider, wine and cocktails are on tap. You’ll find easy-drinking classics like East Kölsch, powerful double IPAs like GigaBoss, dark brews like I Hate Raisins Oatmeal Cookie Imperial Brown Ale, and more.
Eats: The locally sourced, globally inspired, rib-sticking food has become as beloved as the brews. Don’t miss the chorizo and potato empanadas, the Poutine (hand-cut fries topped with homemade gravy and cheddar cheese) and the surprisingly delicious salads.
Fun: The fun is serious here! Show off your arcane knowledge at Trivia Night every Wednesday starting at 7 pm; hit up the mic at Karaoke every Thursday at 7 pm; and come for live music every Friday at 6 pm and Saturdays at 6:30 pm.
405 NY-17M, Monroe, NY
Thursday & Friday: 3-9 pm
Saturday: 1-9 pm
Sunday: 1-6 pm
Apex Brewery was founded by David Holm with help and moral support from his wife, Rachel. The Holms, who love roller derby culture almost as much as they love beer, have decorated their brewery with skating gear—even down to the tap handles made from skate wheels. Expect a Cheers-esque conviviality here.
Drinks: There are usually six creations on tap, typically five seasonal beers and a hard seltzer made in-house. Don’t miss Bones on Wheels if you like a crushable Czech-style pilsner, while Ghost Points Acai Black Currant will hit the spot for fruited Berliner Weisse fans.
Eats: Bring your own or come for mobile food trucks.
Fun: Put your music trivia knowledge to use every Thursday at Music Bingo from 6 pm-8 pm, and weekly trivia sessions on Sundays beginning at 3 pm. On Sundays, Mama Lorusso comes to serve up killer pizza from 1-6 pm. Check the calendar for updates on monthly Music Karaoke, book clubs, comedy shows, and more.
City Winery Hudson Valley
23 Factory St., Montgomery, NY
Wednesday & Thursday 4-9 pm
Friday & Saturday: 11:30 am-10 pm
Sunday: 11 am-9 pm
City Winery Hudson Valley is one of the region’s premier venues, restaurants, wineries and event spaces. Housed in a converted and historic mill, there’s always great drinks and good food on tap—plus plenty of entertainment.
Drinks: Sample award-winning wines made on-site at the 22-acre facility. To learn more about the process, you can sign up for an expert-led tour of the winery, which ends with a flight of housemade wines and a chef-curated plate of local cheese.
Eats: The Barrel Room Restaurant & Wine Bar is rustic and charming, centered around a large central fireplace. Sit down, relax, and dine on globally-inspired, locally-sourced meals. Favorites include the Hudson Valley Cheese Plate and Crispy Fried Chicken Sandwich with smoked paprika aioli and applewood smoked bacon.
Fun: There is always something happening at the winery. Every week through the fall, the Wine Down Wednesday music and wine series takes place from 5pm-7pm with local artists performing on the patio. Also on Wednesdays, Annalyse & Ryan Present: The Songwriters Lounge at 7:30 pm is an immersive concert experience that takes place in The Boiler Room, located in the wine cellar. Laughs Along the Wallkill, a series of comedic performances takes place on Thursdays throughout the summer at 7:30 pm and will leave you laughing. Look for upcoming performances like Hamlet in Gotham City (Shakespeare meets Batman) and Murder Mystery dinners. Check the events calendar for these, and so much more.
Big Dog Brewery
771 State Route 52, Walden, NY
Thursday & Friday: 3-10 pm
Saturday: 12-10 pm
Sunday: 12-6 pm
Big Dog Brewery was founded by rhythm guitarist and singer Tim Santiago and entrepreneur Melissa Raap. The Brewery welcomes well-behaved pets outside when the weather is nice—the Brewery’s own Daniffs (half Great Dane, half Mastiff) Zeus and Althea are often around, too. (Families should note that this is an 18+ year-old venue, no exceptions.)
Drinks: A rotating lineup of seasonal beers is always on tap.
Eats: Come hungry. The brewery schedules food trucks during live music events, but check ahead. (They permit outside food when food trucks aren’t around.)
Fun: As a musician himself, Tim was keen to make live music part of the brewery’s DNA. Rock to live music Friday-Sunday from 7-10 pm, with a $10 cover charge. The best place to catch up on their frequently updated lineup of events is Facebook.
Pennings Farm Cidery
4 Warwick Turnpike, Warwick, NY
Friday: 4-9 pm
Saturday: 1-8 pm
Sunday: 1-7 pm
Pennings Farm has been growing apples for more than 30 years. In 2015, they started fermenting those apples, and the on-farm cidery was born. The complex has expanded with a full-serve pub and grill, and pop-ups like an outdoor beer garden, ice cream stand, and donut shack.
Drinks: Visitors will find a taproom and a hard cider production facility with a regular rotation of about a dozen of seasonal hard ciders at any one time. There is also a selection of local wines, housemade Pennings Vodka (from cider apples) and signature cocktails on the menu.
Eats: Come hungry, because Pennings serves up homemade Neapolitan-style brick oven pizzas topped with locally-grown and seasonal ingredients. (Gluten-free options prepared on a cauliflower crust are also available.)
Fun: Every Thursday at 6:30 pm the cidery holds a Thursday Throw Down. Teams of two compete in a tournament style game of cornhole, and each week one lucky team earns a Pennings Cidery gift card. After cornhole, stick around for Trivia Night. Upcoming special events include live music with the Ethan Levy Duo, and 90s Night with DJ Skyhook. Come for the Sunset Series with Brother Jerome on May 27.
Tin Barn Brewing
62 Kings Hwy. Bypass, Chester, NY
Thursday: 4-9 pm
Friday: 2-10 pm
Saturday: 11 am-10 pm
Sunday: 11 am-7 pm
Tin Barn was founded in 2015 by a father-daughter duo, with the goal of creating the juiciest IPAs in New England. The property is massive with a 12,000 square-foot barn, an expansive two-level deck and live music stage.
Drinks: Come for a range of rotating seasonals on tap, including quirky options like Pleased as Hawaiian Punch, a fruited sour; Unfit for Royalty, a triple New England IPA; or Pushing Boundaries, a sour conditioned on salt peach wine from Funktastic Meads.
Eats: Satisfying beer-friendly snacks (nachos, fried pickles, truffle fries) and pizza (sliced meatball, the shroomy-cheesy Forager) pair perfectly with the brews. Bonus: any pizza can be made vegan.
Fun: Tin Barn is open late with live music every Friday-Sunday. Hours and musicians vary, so check their events calendar for the latest lineup.
Angry Orchard Hard Cider
2241 Albany Post Rd., Walden, NY
Thursday & Friday: 2-8 pm
Saturday: 11 am-8 pm
Sunday: 11 am-6 pm
Angry Orchard’s apple orchard has its roots deep in the past. It has been a working farm since the 1700s, and the first apples were planted there in the 1920s. Angry Orchard purchased the farm in 2015 and began planting cider-making apple trees which now yield exclusive ciders only available onsite. The visitor experience includes tours, outdoor bars, and treehouse tastings.
Drinks: A range of classic and imaginative ciders await, from Hardcore Dark Cherry Apple, an imperial made with dark cherry juice, to Tropical, a juicy pineapple and crisp apple combo, or good old-fashioned Green Apple, a tart but balanced cider that hits all the right spots.
Eats: Angry Orchard serves up delicious snacky fare, perfect for sharing and pairing with cider. Think pesto grilled cheese, wassail sausage and peppers, and apple dumplings to finish.
Fun: Game Nights and Trivia Nights (including themed games, like Disney Trivia) take place on Thursdays and Fridays. Or, book one of Angry Orchard’s rotating experiences, like the exclusive Stone Barn Tasting Experience or the Treehouse Experience with panoramic views of the orchard and the Shawangunk Mountain Range. Keep up to date here.
Find even more after-hours fun on Orange County’s Beverage Trail! You can earn a free Taste the Craft backpack cooler by checking in to five different craft beverage locations on the trail. Check with venues before heading out, though, to make sure the hours listed online are current and that they accept walk-ins.
Now get out there, and have a great time!
Header photo: City Winery Hudson Valley