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50 Things to Do This Summer in Dutchess County
June 7, 2024

By Danielle Page and Will Kirkiles

Dutchess County is the ideal summer retreat, complete with countryside views, small town shopping, and family-friendly activities. Whether you are a year round resident or a seasonal visitor, we’ve compiled a list of the top 50 things not to miss during the summer in the area.

1. Explore the Millbrook Vineyards & Winery for wine tastings, picnics, weekend food trucks, and live music! Millbrook vineyards hosts food trucks & live music on Fridays during the summer season.

2. Go for a bike ride on a local rail trail! The Hudson Valley Rail Trail is a picturesque and family-friendly adventure, stretching 7.1 miles through idyllic hardwood forests. The Harlem Valley Rail Trail spreads 10.7 miles down roads, woods, and fields along the Webatuck Creek.

3. Shop local! The towns of Rhinebeck, Millbrook, Amenia, and Millerton are perfect for small-town strolling and shopping. Check out some of our favorite boutiques:

4. What’s better than a local zoo? Visit red pandas, lemurs, alpacas and more at the Trevor Zoo located on the Millbrook School campus. Don’t forget to make a reservation online beforehand on their website. 

photo credit: Trevor Zoo

5. Hit some balls at the Baird Park Driving Range! In addition to the golf course, the park now also boasts a pro shop, clubhouse, and snack bars at the 1st and 10th holes! (Pleasant Valley)

6. Relax and enjoy the beauty of the Hudson Valley at Innisfree Garden. Innisfree offers plenty of space for hiking, picnicking, and bird watching! Visit their website for info on their guided tours! (Millbrook)

7. Summer in Dutchess County can get pretty hot. Cool off with some of our favorite ice cream at a local scoop spot:

8. Whether you’re an avid hiker or are simply in the mood for an outdoors adventure, the views at the top of Stissing Mountain are well worth a hike! (Pine Plains)

9. Go antiquing! The Northeast Dutchess County area is home to countless quaint antique stores. Here are a few we love:

10. Visit the peaceful Millbrook Tribute Gardens. They have scenic walking paths, benches to sit and enjoy the scenery, and lots of playground fun for the little ones!

11. The Four Brothers Drive In puts a modern spin on a classic drive in movie theater experience. Catch a movie from the comfort of your car and enjoy carhop service from their snack bar! (Amenia)

12. Spruce up your home by exploring some local home goods shops. Here are a few we recommend:

13. Visit a local farmers market. The Rhinebeck Farmers Market, Millbrook Farmers Market, and Millerton Farmers Market offer dozens of local vendors with everything from produce to flower bouquets to baked goods!

14. Explore the hiking trails at the Cary Institute of Ecosystem Studies. You will be immersed in a range of ecosystems, from old fields and upland forests to wetlands. Relax and enjoy the soothing sounds of nature! (Millbrook)

15. Explore the inner workings of local distilleries through tours and tastings. Here’s a few we recommend visiting:

16. Take advantage of the summer weather and dine outdoors. Charlotte’s (Millbrook) is a local favorite with delicious European dishes and a beautiful outdoor patio. Barbaro, located right on Franklin Ave in Millbrook, offers outdoor seating and an irresistible Italian menu. The Amenia Four Brothers Pizza Inn, famous for their greek salads, has a large outdoor seating area perfect for families. Terrapin in Rhinebeck is set in a beautiful converted church and offers exquisite food and excellent patio seating. The Millerton Inn boasts a picturesque porch with lots of seating options. Kips Tavern offers beautiful sunset dinners on the Hudson River, a great selection of cocktails, and a wonderful menu. McEnroe’s Farm on Route 22 in Millerton has an outdoor eatery that is also a lunch spot favorite, and right next to their famer’s market with fresh local produce. 

17. Check out an art exhibition at the Wassaic Project!

18. Saddle up! There are plenty of places to take horse riding lessons, both for adults and kids. Here are some of our family favorite stables:

19. It’s the little things in life. Meet a friend to enjoy a cup of coffee and a bite to eat at a charming small town cafe! Babette’s Kitchen (Millbrook) has delicious drinks and an irresistible pastry selection. Great Cape Baking Company (Amenia) offers homemade breakfast sandwiches, salads, and soups. Irving Farm (Millerton) has some of the best coffee in town! Harney & Sons is a Millerton favorite, complete with a rustic tea room with an extensive choice of world-class blends, plus sandwiches, soups & a terrace.

20. Visit the Old Rhinebeck Aerodrome and take a ride on a biplane or see an airshow! This is an unforgettable experience for all ages.

photo credit: Warren Disbrow

21. Explore the hiking trails at the Dover Stone Church Preserve. This forever-protected 174-acre public preserve, located in the Village of Dover Plains, features more than four miles of hiking trails leading to a natural rock formation called the Dover Stone Church.

22. Relax and enjoy live music at The Millbrook Bandshell, chamber music at The Stissing Center (Pine Plains), or opera, theater, and dance at the Fisher Center. Visit their websites to view their summer concert schedules. 

23. Go fish! Orvis Sandanona boasts a private trout stream and stocked ponds for fishermen of all ages to enjoy. If you’re looking to perfect your cast, check out their website to learn about their 1-Day and 2-Day Fly Fishing Schools. (Millbrook)

24. Take an introductory flight lesson with the Whiskey Foxtrot Aviation School, located right at Sky Acres Airport! They have highly trained, enthusiastic instructors on site that are bound to make you fall in love with flying. (Lagrangeville)

25. Take a skeet shooting lesson at Mountain Valley Farm (Millerton) or Orvis Sandanona (Millbrook).

26. Take a day to explore all the art galleries the area has to offer! Here are a few worth checking out:

27. Enjoy the beautiful scenery of the Hudson Valley at the Wethersfield Estate & Garden. Explore three acres of formal Italian garden and seven acres of wilderness garden, or hike their trails. (Stanfordville)

photo credit: Yoshi Tano

28. Go see a film at the Millerton Moviehouse or Upstate Films. They feature current films, classic films, and often host film events!

29. Head to Kelly’s Creamery for ice cream, a food truck, and 18-hole mini golf… fun for the whole family! (Dover Plains)

30. Dive in! Go for a swim in Stissing Lake at the Stissing Lake Park, located right in Pine Plains.

31. Skate back to the 80’s at Roller Magic. (Hyde Park)

32. Catch an enthralling play at the Tivoli Theater.

33. Take a stroll over the “World’s Longest Elevated Pedestrian Bridge”: the Walkway Over the Hudson, and take in the views. (Poughkeepsie)

34. Grab a sandwich from one of Dutchess County’s favorite delis:

35. Visit the Francis Lehman Loeb Art Center and explore Vassar College’s extensive collection of classic and contemporary artwork. (Poughkeepsie)

36. Pick up a new LP to jam out to at Darkside Records. (Poughkeepsie)

37. Cheese, please! Visit Beacon Cheese Shop or Cheese Louise (Rhinebeck) to craft the perfect charcuterie board.

38. Visit and tour an estate! Dutchess County offers the elegant Vanderbilt Mansion and the stately Home of Franklin D. Roosevelt in Hyde Park. Also check out the beautiful Victorian Mansion at the Wilderstein Historic Site.

39. Eat some comfort food at a local diner:

40. Check out cool modern art at the Dia Museum. They have an on-site cafe! (Beacon)

41. Enhance your style with some outdoor clothes at Westerlind. (Millerton)

42. Visit Bannerman Castle for a tour, a fine meal, or a play! It’s on an island! (Fishkill)

43. Visit Washington’s Headquarters, where the nation’s first president made crucial decisions about the future of the country! (Newburgh)

44. Walk your dog, do some yoga, or simply contemplate amongst the beautiful scenery at Poet’s Walk Park. (Red Hook)

45. Take a free tour of Eleanor Roosevelt’s beautiful Stone Cottage and learn about the important meetings that took place at this historic site. (Hyde Park)

46. Beat the heat with a guided Kayak exploration of the Hudson River with Atlantic Kayak Tours. (Tivoli)

47. Grab a drink and play classic video games at Happy Valley Arcade Bar. (Beacon)

48. Go climbing! The Gravity Vault offers day passes with staff instruction to help you develop your climbing skills! (Poughkeepsie)

49. Who doesn’t love a good fair? The Dutchess County Fair in August is a chance to experience rides, live music, animals, local crafts, and more! (Rhinebeck)

50. Craving a sweet treat? Go to Glazed Over Donuts and check out the Donut Ice Cream Sandwich. (Beacon)