Throughout the Fall: Concerts in the Vineyard

Sit back and relax, with a glass of your favorite red and sultry tunes. Jam out to artists like The Weight Band, Spin Doctors, and Suzanne Vega at City Winery’s vineyards (above), surrounded by beautiful fall foliage.

City Winery, Montgomery; citywinery.com/hudsonvalley

Throughout the Fall: Foliage Wine Tour

Dive deep into wine pairings with local vintages, artisanal cheeses, and colorful autumn scenery. Hudson Valley Bucket List will take you on a six-hour shuttled tour to three vineyards around the region to sample wines and local cheeses. These historic cellars and picturesque views will not disappoint.

Beacon-based; hvbucketlist.org

September 11–12: Hudson Valley Wine & Food Fest

Find a smorgasbord of delicious bites presented by a range of gourmet vendors, including Sherri’s Crab Cakes food truck and Corey’s gourmet pickles. Attend a cooking or wine seminar taught by some of the best in the business.

Dutchess County Fairgrounds, Rhinebeck; hudsonvalleywinefest.com

September 18: 7th Annual Hudson River Craft Beer Festival

Along the scenic Hudson River in Beacon, sample over 180 craft beers from over 90 of America’s best craft breweries while enjoying live music, local vendors, and delicious food. And if you’re willing to splurge, there will be VIP admission.

Beacon; americaontap.com

October 23–24: Boos & Brews

Halloween is arguably the best time of year to spend in an orchard. Full of autumnal cheer and seasonal treats, Barton Orchards hosts a weekend of tricks and treats, including haunted houses, jack o’ lantern trails, hayrides, and apple and pumpkin picking. Don’t miss out on the live music and excellent ciders from their taproom.

Barton Orchards, Poughquag; bartonorchards.com

November 4: Dutch Ale House Beer Pairing Dinner

Winner winner, beer and dinner. The Dutch Ale House is treating guests to a creative four-course menu paired with craft beers from the iconic West Kill Brewing, for $70 a head. Tickets must be purchased in advance.

Dutch Ale House, Saugerties; dutchalehouse.com/tickets