Top 10 Activities for Every Generation to Enjoy Together

Date Published: August 6, 2019

Whether it be for a family reunion, or just a fun day out with family, Dutchess County offers so many options for every generation to enjoy together. Check out these ideas for family-friendly activities in Dutchess and plan your visit today!

1. See a Movie at the Drive-In

Drive-ins may be a dying activity throughout the country, but not here in Dutchess! There are two main drive-in movie theaters that should be on your radar. Four Brothers Drive-In in Amenia gives you a great feeling of nostalgia with throwback decor and car hop service. Overlook Drive-In in Poughkeepsie is your classic, no-fuss drive-in experience that features the largest screen in the tri-state area.

2. Cheer on the Hudson Valley Renegades at Dutchess Stadium (Seasonal)

There is nothing like a Renegades game on a warm summer night at Dutchess Stadium in Wappingers Falls. Make this night even more special by sharing it with your family! Children and adults alike love this atmosphere of ballpark snacks, on-field games, and some all-American baseball.

Click here for ticket information!

3. See the Animals at Trevor Zoo

A truly unique experience awaits at Trevor Zoo, America’s only AZA accredited zoo located at and ran by a high school. Students from Millbrook School care for more than 180 exotic and indigenous animals including eight endangered species. Highlights include red pandas, lemurs, wallabies and bobcats. Meeting the students and the animals in this intimate zoo setting is a memorable experience for anyone who visits!  For more information and to plan your visit, click here. 

4. Witness the WWI Planes at Old Rhinebeck Aerodrome

The entire family is sure to love a trip to the Aerodrome to see some antique aircrafts and explore the museum. Although the museum is open anytime, come on the weekends between June to October to experience a Pioneer era airshow on Saturday and a World War I airshow on Sunday. If any one of your family members is a thrill seeker, they can arrange to fly in a 1929 biplane alongside an experienced pilot, which is sure to promise great views of the county.

Click here for more information and airshow times!

5. Pick-Your-Own at Fishkill Farms 

Fishkill Farms is a fantastic pick-your-own destination. With harvest festivals every weekend in the fall, this place will give you some serious autumn vibes. There are many events throughout the year including “Peachtopia” in August, and Yoga on the Farm every Saturday from June to October. There is a historic element to this farm because Henry Morgenthau Jr. founded the farm in 1913, and went on to be Secretary of the Treasury during Franklin Delano Roosevelt’s presidency. The Treasury Cider Garden is named for this, where adults can taste and purchase hard cider grown on the farm. Everyone in the family is sure to love this classic pick-your-own.

For seasonality of produce, click here.

6. Brunch at Shadows on the Hudson

Shadows on the Hudson in Poughkeepsie is great for hosting large parties if you call in advance. Their brunch buffet is to-die-for and can accommodate even the pickiest eaters in your family. With views of the Hudson River and surrounding mountains ranges it is particularly nice during warmer months when they offer outdoor seating!

Click here for more information.

7. Take a Stroll on the Walkway Over the Hudson

The Walkway Over the Hudson in Poughkeepsie is the perfect activity for some family fun, while squeezing a little bit of exercise in. The views are unbeatable and it is a great way to enjoy some outdoor time with loved ones. The Walkway is a converted railroad bridge dating back to 1889 that has been adapted and reused as a 1.28-mile long walking and biking trail that is a part of the Dutchess Rail Trail. It is the longest elevated pedestrian bridge in the world. There are plenty of benches along the way to sit and enjoy the view. In 2012, a world record was set on The Walkway for the most people doing the Hokey Pokey! Come to the Walkway and do your own Hokey Pokey in this legendary spot.

8. Marvel at the History of Staatsburgh State Historic Site

Staatsburgh is a prime example of an estate built by one of America’s financial and industrial moguls in the Gilded Age. This 79-room features elegant rooms of lavish proportions. Come learn about the history of New York and surround yourself with beautiful grounds and views. The mansion tour is roughly an hour, but call in advance and ask about the special themed torus, Tea and Talk Series, and children’s programming offered.

Click here for more information.

9. Picnic at Innisfree Garden

Check out this hidden gem in Millbrook. Come and be one with nature in this masterfully designed, world-renowned gardens. Innisfree has been recognized as “one of the world’s ten best gardens”. You can even coordinate with monthly guided wildflower tours for an added educational element. There is a designated picnic area with tables to make your picnic perfect. Kids will love running in the wide-open spaces and looking at the wildlife in the pond. Bring lunch, a good book, and come find your Zen!

Learn more here.

10. Explore the Village of Millerton

Millerton is a small village, but it has some great shops and activities that will please everyone. Come sample some artisanal Harney and Sons Fine Teas, and stay for lunch at their café. Choose from a delectable menu of tea-inspired dishes, including tea infused cheeses. These teas are a unique gift idea for friends back home because the tasting room carries more flavors than what you would find in your grocery store. Millerton is also home to the Harlem Valley Rail Trail, which is the perfect opportunity to take a family walk or bike ride. The Oblong Books & Music Store has a kids room that will get your little ones excited about reading.

Bonus: Ice Cream and Mini-Golf at Kelly's Creamery

For lunch, Kelly’s Creamery and Kelly’s Husband Food Truck is a wonderful piece of family trips in the Hudson Valley. This roadside paradise serves fun grill fare, including burgers, brats, veggie sandwiches, hot dogs and more—usually with a few exciting twists. Kelly created over 30 flavors of artisanal ice cream, soft serve and Italian ice. This Dover Plains destination also features a sprawling 18-hole mini-golf course, a bocce court and other enjoyable activities.

Contact Dutchess Tourism for help planning your family trip today!