Spring is here–thank goodness–and Dutchess County is bursting with possibilities! From cuddly lambs at Black Sheep Hill Farm in Pine Plains to dazzling cherry blossoms at Dassai Blue Sake Brewery in Hyde Park, there’s a little magic waiting around every corner. Explore charming boutiques, sip spirits at local distilleries, wander stunning gardens, and catch lively performances at the Stissing Center or Wassaic Project. Whether you’re craving a glamping adventure at Hotel Caravana, strawberry picking at Fishkill Farms, or a nostalgic double feature at the Four Brothers Drive-In, this curated list of 25 springtime experiences promises something fun, fresh, and unforgettable for everyone. Dutchess County isn’t just a destination—it’s a season of adventure. 🌱🌷
1. Being a black sheep can be a bad thing but not if it’s one of the flock at Black Sheep Hill Farm in Pine Plains. Visit the farm store, buy some yarn, and maybe cuddle some lambs.
2. It would be a shame for the sprawling Dutchess County Fair grounds to be empty until the annual autumn harvest fair. Good thing, then, that the grounds in Rhinebeck are busy all through the spring and summer, with exciting events like car shows, spring fling bazaars, and craft fairs!
3. Walkway Over the Hudson has plenty of events throughout spring and summer, but is also a perfect spot for a casual stroll with friends and family; take in the serenity of spring and panoramic views from the bridge.
4. Visit Troutbeck in Amenia for a picturesque getaway experience. Guests can enjoy the tennis court, walled garden, pool, and relaxing procedures at the spa.
5. The Sheep and Wool Showcase in Germantown has the distinction of being the first in the wool festival season! This family-friendly festival offers spinning and weaving demonstrations, sheep herding and shearing, and a shopping concourse featuring work from artisans and craftspeople. The festival takes place on April 25, 11 am – 4 pm. Cost is $15 per vehicle.
6. Innisfree Garden, tucked away down a dirt road in Millbrook, has a remarkable collection of daffodils, open for all to view on April 25! Consider becoming a member of Innisfree so you can enjoy not just the daffodil display but other magical events such as Morning Light: Sunrise at Innisfree, held on Saturday, May 9.
7. Check out the Stissing Center in Pine Plains. April and May include musical performances by The Tom Duffy Band, Bees in the Barn, Amanda Forsyth. Enjoy lively performances too, such as Puppet Slams, Tablao Flamenco, and The Bang Group.
8. Book a luxurious glamping trip at Hotel Caravana, located on site of the Four Brothers Drive-In in Amenia! Complete with room service, mini golf, private outdoor lounge area, and, of course, a double feature movie showing.
9.The Old Rhinebeck Aerodrome opens back up for air shows starting June 20! The working airfield and museum offer old and young enthusiasts a chance to learn about the thrilling first days of flight in a hands-on setting. Flights and air shows are offered on weekends, usually between 10 a.m. and 2 p.m. Visitors on weekdays might see test flights; and the mechanically minded might get a chance to chat with mechanics working on the historic planes.
10. History buffs and fans of the 1997 film can celebrate the legacy of the Titanic in Staatsburg by visiting the grand home of ticket holders, Ogden and Ruth Mills. The 90-minute Tales of the Titanic: Themed Mansion Tour features harrowing stories from the Titanic’s voyage and explores the connection between the opulent mansion rooms and first class appointments aboard the ship.
11. Wethersfield Estate and Gardens in Stanfordville won’t officially open to the public until May, but here are two opportunities to enjoy the grounds and spectacular trails before then. An Educational Bird Walk on May 29 will be hosted by The Waterman Bird Club, and for horseback riders a Spring Conditioning Ride on May 9. The Gardens officially open to the public on May 29.
12. Check out Dassai Blue Sake Brewery’s Annual Cherry Blossom Festival in Hyde Park! An open house event, free to the public, with food vendors and local craft & art vendors. Picnic under the gorgeous cherry blossom trees on site and take in the beauty of springtime.
13. Save the date for Dutchess Land Conservancy’s Spring Barn Dance! Dust off your boots, round up your friends, and join DLC for a night filled with music, laughter, dinner, and dancing. Saturday, May 16 at Silver Mountain Hay Barn in Millerton.
14. Visit Fishkill Farms for a delicious brunch, to grab homemade products from the farm store, or to pick-your-own strawberries starting in June. Be sure to grab some of their famous apple cider donuts from the farm store!
15. Mashomack Polo Club, nestled on a 2,000-acre preserve in Pine Plains, hosts exciting polo tournaments from June through September. The club also hosts a full array of polo school services, including lessons, developmental polo leagues, junior polo, and ladies’ tournaments.
16. Greig Farm in Red Hook also has strawberry picking in June, as well as fresh seafood markets on Saturdays, and feed-the-goats and walk-the-farm activities for all ages!
17. The Four Brothers Drive-In in Amenia will be kicking off their season starting late March. Enjoy first-run films, classic throwback showings, and celebrity events! Not only is there a full-service restaurant on site, but also a gourmet snack bar complete with popcorn, candy, burgers, hot dogs, lobster rolls, milkshakes, sundaes, and more! All films begin at sundown.
18. Montgomery Place Orchards in Red Hook will enter its 40th season when they reopen in May. Purchase fresh fruits and vegetables from the market, historically known as the “Wayside Stand.”
19. Visit the Wassaic Project in Wassaic exhibition openings, artist talks, open studios events, and summer benefits! Browse brilliant work from emerging artists, like at their 2026 Summer Exhibition Opening, on May 16.
20. Visit the Tenmile Distillery in Wassaic for distillery tours and spirit tastings. Or just stop in for lunch or dinner at Thai Baan, and grab a drink at the Tenmile Bar.
21. Kitschy and delicious Del’s Roadside sells small-batch ice cream made from its own 300-acre dairy farm, on Albany Post Road in Kingston. The old-fashioned eatery also has burgers and other warm weather standards.
22. Take a beautiful spring walk on the Harlem Valley Rail Trail, spanning from Wassaic, through Millerton, all the way up to Chatham. Springtime is the perfect time to get out, get some fresh air, and appreciate nature in its truest form after a long, harsh winter.
23. Stop in to the iconic Samuel’s Sweet Shop on Main Street in Rhinebeck, and you might be able to get candies imprinted with the faces of your favorite actors. While in Rhinebeck, get a non-sweet snack across the street at the restaurant of Bread Alone Bakery. The whole family can walk just a little farther up the road to see the historic Rhinecliff-Kingston Amtrak train station.
24. Northern Dutchess Botanical Gardens sounds like another garden to tour and be inspired by. In fact, it is a nursery in Rhinebeck selling an incredible variety of annuals, perennials, and organic edibles. It’s a bit of a gardener’s secret, and apologies to the friend who turned us onto it, but really this is a secret too good not to share.
25. Located just south of Pine Plains on Route 82, Buttercup Farm Audubon Sanctuary boasts 641 acres of diverse habitats for over 80 species of birds. Visitors can enjoy six miles of walking trails throughout rolling, picturesque grasslands where they may spot great blue herons, bobolinks, and golden-winged warblers. Leashed dogs are welcome on the trails.