Here are 30 things to do in Dutchess County for your next vacation.

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, one of the stops on the DCSWGA Farm Tour on April 12. 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 such as the April “ENY Cattle Preview” and Antique car show and swap meet and the Spring Antiques show.

 

3. What better way to spend a spring evening than strolling the streets of Rhinebeck enjoying tasty treats? The Taste of Rhinebeck brings together bites and sips from local restaurants, spirit shops, and specialty stores along a walkable path that winds through the streets of historic Rhinebeck Village. The event takes place on May 7th. Tickets must be purchased in advance. 

 

4. Get your hands dirty and do good at the same time. The Dutchess Land Conservancy in Millbrook has many volunteer opportunities. Sign-up for the Seven Wells Volunteer Trail Work Day in Millbrook on April 26. Wear weather appropriate clothing and bring snacks + water. 

 

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 26, 11 am – 4 pm. Cost is $12 per vehicle. 

 

6. Daffodils at Innisfree Garden, This Chinese-inspired garden, tucked away down a dirt road in Millbrook, has a remarkable collection of daffodils all planted more than 60 years ago. Consider becoming a member of Innisfree so you can enjoy not just the daffodil display but magical events, such as Morning Light: Sunrise at Innisfree, held throughout the summer.

7. Check out the Stissing Center in Pine Plains. The offerings in the month of April include performances by Lonesome Ace String Band, Diana Byer and Dancers and a Hudson Valley puppet slam. Every month brings a selection of eclectic offerings. 

 

8. The Old Rhinebeck Aerodrome Fly back to the days of the golden age of aviation on the wings of a 1929 biplane, with a visit to the Old Rhinebeck Aerodrome (which opens May 1). 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. Keep in mind that these old engines can be noisy and there are occasional combustion explosions that might frighten young children.

 

9. 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. Check for availability April 12 through April 26.

 

10. Wethersfield Estate and Gardens in Stanfordville won’t officially open to the public until June, but here are two opportunities to enjoy the grounds and spectacular trails before then. An Educational Bird Walk on May 23 will be hosted by The Waterman Bird Club, and for horseback riders a Spring Conditioning Ride on May 10. The Gardens officially open to the public on June 8. If you have never visited Wethersfield, you owe it to yourself! 

11. Get spring planting advice from the pros at Cornell Cooperative Extension’s annual Master Gardener Spring Plant Sale, Friday, May 16 (10 am – 4 pm) and Saturday, May 17 (9 am – 2 pm). Choose from an amazing selection of annuals, perennials, vegetables, and herbs grown by Master Gardener volunteers. Proceeds fund CCE’s educational programming. Volunteers will be available to answer gardening questions, help with plant selections, and even take plants to your car. Dutchess County Farm & Home Center, 2715 Route 44, Millbrook. 

 

12. An old favorite returns. The DLC Road Rally is back! Support the organization that is responsible for stewarding more than 46,000 acres of forest and farmland in Dutchess County, and have a foot-stomping great time while you’re at it. Saturday, May 17, spectacular vintage cars, two Incredible Driving Routes, and a celebratory Luncheon at the Amazing Tenmile Distillery in Wassaic. Get tickets by calling the Development Office. They’re not available online.

 

13. Starting the first week of June some of us anxiously check the Facebook posts of Thompson-Finch Farm (organic berry farm on Wiltsie Bridge Road in Ancram) trolling for the ripeness status of the berries. Some of us also save our berry baskets from the year before. And when the picking is good, there is nothing more satisfying than putting on some sunscreen, grabbing your straw hat, and making for the fields dreaming of strawberry shortcake, strawberry rhubarb pie, or just strawberries and vanilla ice cream—not to mention the ones you must sample as you make your way down the rows.

 

14. Mashomack International Polo Challenge and Luncheon on Saturday, June 21 in Pine Plains. You don’t need to understand the rules of the game to enjoy a champagne lunch and ringside seats to the fast-paced action. Of course, the people-watching is as much a part of the fun, and if you don’t arrive sporting a big-brimmed hat, there will be opportunities to buy one. And speaking of buying, this event sells out early, so if you’re interested, don’t wait till the week before. (No General Admission, everyone must have a ticket to the Fieldside Luncheon)

15. Greig Farm in Red Hook for farmstanding and strawberry picking in June (they have asparagus starting in May).

16. Mention the drive-in movie theater in Amenia to anyone who isn’t familiar with it, and they’re likely to ask if the screenings are of vintage films. The Four Brothers Drive-in, which is run by the younger members of the family that owns the ubiquitous Four Brothers restaurant chain, primarily screens first-run films (although from time to time the local Boondocks Film Society will show older cult films). A tasty bonus of Four Brothers Drive-in shows: Of course there’s popcorn but movie patrons can also access the full menu at the restaurant and the summer ice cream and hot dog stand. All films begin at sundown.

17. Spring is a bit too early to get fresh farm-grown produce at the Montgomery Place Farmstand in Red Hook on Route 9G, but it’s never too early or late to visit the nearby 380-acre Montgomery Place estate (a National Historic Landmark, which has been owned by nearby Bard College since 2016). One of the many historic and often lavish estates that are open to the public in the Hudson River Valley, Montgomery Place is less famous than such better-known properties as Olana, the Rockefellers’ Kykuit and the two former Roosevelt homes. Agriculture is one of the main draws to Montgomery Place, with gardens planned by Andrew Jackson Downing (as well as acres and acres of orchards). The mansion at Montgomery Place was designed by architect Andrew Jackson Davis. The land was purchased in the 1850s by Janet Livingston Montgomery, who created the estate — one of the few Hudson River estates that was run by a woman. Touring historic estates can bring up uncomfortable questions about history in this era of accountability; because property owner Bard College encourages its students to be socially conscious and thoughtful, the Montgomery Place tour information is refreshingly upfront and honest about slavery and other topics of concern.

 

18. GioBatta Alimentari in Tivoli is the new iteration of the formerly beloved Red Hook eatery called Mercato (famous for, among other things, its lacinato kale salad) owned by husband and wife/chef team Francesco Buitoni and Michele Platt. The couple closed Mercato in about 2021 and reopened in nearby Tivoli as GioBatta. Chef Buitoni is from the family that started the famous Buitoni Italian food line; and he has competed in “Beat Bobby Flay.” Mercato was nominated for two James Beard awards. GioBatta continues with many of the favorite foods from Mercato, and more. It is open Wednesday through Sunday.

 

19. There is a universe of entertainment options at the Bardavon Theater in Poughkeepsie and its sister venue, the Ulster Performing Arts Center (aka UPAC), with live performances coming this spring. If you’re going to Bardavon and feel adventurous, Poughkeepsie is the center for authentic Mexican food in Dutchess County; most restaurants are small hole-in-the-wall type eateries.
20. Hudson Hall in Hudson is a renovated historic theater with everything from a respected annual jazz festival to drag shows to exhibitions of contemporary art to screenings of vintage and contemporary films. 

 

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. Learn to cook seasonal foods (or just “sharpen” your knife skills) at a cooking class at the Hillsdale General Store.  The little village of Hillsdale has become a mecca of chic niftiness in recent years; it’s worth a day trip to visit the General Store, the super stylish Tiny Hearts Flower Shop and the Roe-Jan brewery and “pantry.”

 

23. The iconic Samuel’s Sweet Shop on Main Street in Rhinebeck was in danger of closing down a few years ago; several local families stepped in to save it, including the families of actors Paul Rudd and Jeffrey Dean Morgan. Stop in to see what all the fuss is about, 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 (which is still in use and sits on the shores of the Hudson River). 

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. One of the most spectacular panoramic views in the Hudson Valley can be found at the top of Burger Hill, a 550-foot hilltop that’s part of Drayton Grant Park on Route 9G, just outside of Rhinebeck. After tackling the short, invigorating walk up the hill, you’re rewarded with breathtaking views of the Shawangunk Ridge, Catskill and Taconic mountains, Stissing Mountain and the Berkshires, way off in the distance. It’s also a great outing for kids and dogs.

 

26. Hikers, bikers, ramblers, amblers, and dog-walkers (on the leash, of course) all share the Harlem Valley Rail Trail. This 26-mile long trail runs from north of the hamlet of Wassaic into Columbia County, passing through the towns of Amenia and Millerton There are many points along the way to access it. Of course if you park in Millerton you can reward yourself with some refreshment from any of a long list of choices: Harney & Sons Fine Teas; Oakhurst Diner; Irving Farm; the market downstairs at Westerlind to name a few. In Amenia, many people make a stop at Fudgy’s Ice Cream (on Route 22) the reason for going. 

 

27. As any parent knows, summer camps fill-up fast. So now is the time to sign up your little equestrians. MLC Farm on Little Rest Road in Millbrook has posted its summer camp schedule on Facebook. Dates in July and August. For ages from 6-16. 

 

28. 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. 

 

29. Stony Kill Farm in Wappingers Falls has open barn hours from February through November on Saturdays and Sundays, from 11 am – 1 pm. Visitors have the chance to meet the animals up close on a tour led by the farm’s volunteer barn guides. The tour is free to the public, and children must be accompanied by an adult.
30.  Spring into spring with something new and kicky from Juniper Boutique in Millbrook. Exquisite gifts, tableware, jewelry, linens, handbags, stationery, toys, and eye-catching fashions for women, men, and kids—it’s all there and it’s all beautiful. Plus, Lisa behind the counter is incredibly friendly and a wiz at wrapping your gift purchases.

By ML Ball, Laura Hartle, Cynthia Hochswender, and Tara Kelly