Quaint & Crafty in the Hudson Valley: 25 Things to Do with Kids in Rhinebeck

About 100 miles north of Manhattan, the quaint town of Rhinebeck in Dutchess County is a prime destination for a family day trip with enough attractions to justify even a longer stay. Steeped in Dutch history, Rhinebeck is home to the Dutchess County Fairgrounds, where numerous fairs and family-friendly productions are held annually, as well as a performing arts center, an aerodrome, the oldest hotel in the country, great eateries, family shopping and nature excursions.

We've gathered up some of our favorite Rhinebeck attractions culled after a recent visit. These include both year-round opportunities and some seasonal excursions, as well as a sampling of the creative shops and eateries that remind visitors of the quaintness afforded by a town supportive of independently owned businesses.

Read on for our inside scoop on all the great fun that lies ahead for your family in beautiful Rhinebeck! And for more great days out, check out our guide to family fun in Hudson Valley.

It's true -- George Washington slept here!

1. Spend the night in the historic Beekman Arms, the oldest continuously operating inn in the U.S. George Washington was a guest.

2. Dine at the Foster’s Coach House Tavern, in operation since 1890.

There are weekend air shows through October at the Rhinebeck Aerodrome.

3. See a World War I air show, view historic aircraft and fly in a biplane at the Old Rhinebeck Aerodrome.

4. Take in a live show at the Family Entertainment Series, offered most Saturday mornings, at the Center for Performing Arts at Rhinebeck.

5. Camp, hike, picnic, ski, bike or climb the tower at the 200-mile Ferncliff Forest Game Refuge and Forest Preserve.

6. Go sledding, hiking and more at the Drayton Grant Park at Burger Hill.

Kids can stretch out and enjoy a good book at Oblong Books & Music.

7. Find great selections for kids (and adults) at Oblong Books & Music, offering books, toys, and gift items.

8. Shop the eclectic five-and-dime at A.L. Stickle Variety Store (aka Stickles).

9. Enjoy a full-blown fair, replete with livestock competitions, carnival rides, food, racing pigs, a petting zoo, a roving robot and much more at the Dutchess County Fair.

10. Bounce a three-mile course at the Insane Inflatable 5K.

11. Snag a burger, fries and a shake at Del’s Dairy Creme.

12. Meet the animals, watch demonstrations and participate in cool wool-related workshops for kids at the annual Sheep and Wool Festival.

13. Take a pony ride or horseback riding lesson at the Southlands Foundation.

The only trouble with Bread Alone is having to choose.

14. Dine at the family-friendly Bread Alone Bakery & Café, where breakfast, lunch and the bakery items are all top-notch.

15. Pay a visit to the 19th-century Wilderstein Historic Site (which gets decked out for the holidays in November and December).

16. Pick apples and pumpkins at the Cedar Heights Orchard.

17. Catch a film or special event at the artsy (and low-priced) Upstate Films.

18. Shop for handmade crafts and meet the artisans at the Rhinebeck Crafts Festival.

19. Buy local from Hudson Valley purveyors at the Rhinebeck Farmers Market where you can snatch some delicious tacos.

A small sample of the selections at Land of Oz.

20. Watch eyes widen at the Land of Oz Toys & Gifts.

21. Be a kid in a ... well, you know, at the Samuel’s Sweet Shop (co-owned by a pair of familiar faces).

22. Sample the selection at Oliver Kita Chocolates.

23. Soak up the holiday spirit at the effervescent Sinterklaas Festival Day.

24. Venture slightly south to Hyde Park for FDR, CIA and other family attractions.

25. Head slightly further to Poughkeepsie for the Walkway over the Hudson, cultural events at Bard and Vassar Colleges, and the Mid-Hudson Children’s Museum.

All photos by the author

A.L. Stickle Variety Store
13 East Market Street
Rhinebeck, NY 12572

Beekman Arms
6387 Mill Street
Rhinebeck, NY 12572

Bread Alone Bakery & Café
41 East Market Street
Rhinebeck, NY 12572

Cedar Heights Orchard
Crosby Lane
Rhinebeck, NY 12572

Center for Performing Arts at Rhinebeck
661 Route 308
Rhinebeck, NY 12572

Del's Dairy Creme
6780 Albany Post Road
Rhinebeck, NY 12572

Drayton Grant Park at Burger Hill
3137 New York 9G
Rhinebeck, NY 12572

Dutchess County Fairgrounds
6550 Springbrook Avenue
Rhinebeck, NY 12572

Ferncliff Forest
68 Mt Rutsen Road
Rhinebeck, NY 12572

Foster’s Coach House Tavern
6411 Montgomery Street
Rhinebeck, NY 12572

Land of Oz Toys & Gifts
41 East Market Street
Rhinebeck, NY 12572

Oblong Books & Music
6422 Montgomery Street
Rhinebeck, NY 12572

Old Rhinebeck Aerodrome
Stone Church Road & Norton Road
Rhinebeck, NY 12572

Oliver Kita Artisan Chocolate
18 West Market Street
Rhinebeck, NY 12572

Samuel’s Sweet Shop
42 East Market Street
Rhinebeck, NY 12572

Upstate Films
6415 Montgomery Street
Rhinebeck, NY 12572

The Southlands Foundation
5771 Route 9
Rhinebeck, NY 12572

Wilderstein Historic Site
330 Morton Road
Rhinebeck, NY 12572
City Skate Pop-Up Concert
Bryant Park - 1:00 PM Pick
Monuments Now
Socrates Sculpture Park - 9:00 AM
Skyline Drive-in
Skyline Drive-In - 9:00 PM
Brooklyn Bridge Park - various times
Intrepid Adventures: Intrepid Women
The Intrepid Sea Air and Space Museum Online - various times
Neighborhood Guides
Activity Guides