1. Explore the Millbrook Vineyards & Winery for wine tastings and picnics (weather permitting). Enjoy their Souper Chef weekends every Saturday and Sunday from November-March. 

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

3. 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 at millbrook.org/plan-your-visit/hours–admission.

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

1. 1. Shady Knoll
   2. Taconic Distillery
   3. Tenmile Distillery
   4. Hillrock Distillery

5. Whether you’re an avid hiker or are in the mood for an outdoors adventure, the views at the top of Stissing Mountain are well worth the hike!

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

1. 1. Millbrook Antiques Mall
   2. Millbrook Antique Center
   3. Apple Antiques
   4. Amenia Station
   5. Bowen Barn Antiques
   6. Bulls Head Treasure
   7. Hunter Bee
   8. Montage Antiques

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

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

1. 1. Lucky Orphans Horse Rescue (Dover Plains)
   2. Rivendell Riding Academy (Clinton Corners)
   3. MLC Stables (Millbrook)
   4. Riga Meadow at Coole Park (Amenia)

9. 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 has delicious drinks and an irresistible pastry selection. Great Cape Baking Company offers homemade breakfast sandwiches, salads, and soups. Irving Farm 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 and soups.

10. 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. 

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

1. 1. Belvoir Gallery
   2. Fine Home Source
   3. The Re Institute
   4. Geary
   5. Blueberry Hill Galleries
   6. Albert Shahinian Fine Art/Upstairs Galleries
   7. Studio 44
   8. Mad Rose Gallery
   9. Dia Beacon
   10. Betsy Jacaruso Studio and Gallery
   11. Frances Lehman Loeb Art Center

12. Poets Walk is the perfect, pet friendly, afternoon stroll after a morning in Rhinebeck. Take in the beautiful Hudson River scenery!

13. Enjoy an evening out at The Moviehouse in Millerton to watch a range of movies, including the Met Live performance of AIDA. January 25, 2025.

14. Go sporting clay shooting at Orvis Sandanona in Millbrook. If you’ve never shot sporting clays before, sign up for a lesson before going out on the course!

15. Tour Franklin D. Roosevelt’s childhood home and Presidential Library in Hyde Park.

16. The Hessel Museum of Art at Bard College is open to the public Wednesday-Sunday. Reservations are encouraged!

17. Who doesn’t love cuddling cute cows? Elk Ravine Farm in Amenia offers farm tours year-round to see their Scottish Highland Cows and horses! Reservations are required.

18. Attend Transcription As Translation at Bard College on February 8-9, 2025. Tickets are required.

19. Looking for a new way to stay active? Check out Forza in Millbrook! Forza Fitness and Training offers both in person and virtual classes.

20. Try your hand at pottery making at Hudson Valley Pottery in Rhinebeck!

21. Curl up with a good read at one of Dutchess County’s independent bookstores like The Merritt Bookstore in Millbrook, Oblong Books in Millerton and Rhinebeck, and Binnacle Books in Beacon.

22. Go ice fishing at a local lake or pond, but please read about ice safety before you go.

23. Sip brews at Dassai Blue Sake Brewery in Hyde Park, Lasting Joy Brewery in Tivoli, From the Ground Brewery in Red Hook or Mill House Brewing Company in Poughkeepsie.

24. Visit one of these gorgeous decorated historic sites for the holiday season!

1. Staatsburgh State Historic Site in Staatsburgh
2. Wilderstein Historic Site in Rhinebeck
3. Mesier Homestead in Wappingers Falls
4. Clermont State Historic Site in Germantown
5. Locust Grove in Poughkeepsie
6. Vanderbilt Mansion in Hyde Park

25. Stop by Stissing Center in Pine Plains for some live music and shows this winter season.