2022 Summer Event Calendar in the Hudson Valley

2022 Summer Event Calendar in the Hudson Valley

  • HW Guernsey Realtors, Inc.
  • 06/20/22

New York City may be known as the city that never sleeps, but there’s plenty in Hudson Valley to keep you awake. The region loves special events, from cultural performances and food and wine to sports-related activities. As the weather warms up, there’s no reason you should ever be bored at home. Don’t miss some of these hot events this summer.


Tequila and Taco Tasting

June 3, 2022
Sleepy Hollow

Learn the differences between white and gold tequilas and why the agave-based liquid complements spicy tacos at the Tequila and Taco Tasting workshop. Hosted at the Hudson Valley Writers Center, attendees can learn more about tequila itself, some recipes for tequila cocktails, and tequila pairing. It’s a fun way to spend an evening and meet some new people.

Kaatsbaan Summer Festival

June 3-91, 2022

Immerse yourself in the arts at the Kaatsbaan Summer Festival. See live dance performances, listen to music, hear poetry, and view stunning sculptures. Even the culinary arts are represented at the festival.

Strawberry Festival - June 5, 2022

June 5, 2022
Hopewell Junction

Strawberries perfectly represent summer, and the Strawberry Festival is a magical summer event. Living history demonstrations pay tribute to New York’s origins, and hayrides, crafts, and music provide plenty of modern-day entertainment. Of course, there’s also the food! In every shape and form, strawberries can be found, from shortcakes to lemonade.

Beer, Bourbon, and Bacon at Barton Orchards

June 5, 2022

Beer, Bourbon, and Bacon — is there anything people love more? This event centers around exploring the flavors of these beloved items with innovative recipes prepared by favorite local restaurants. The dog-friendly festival allows people to enjoy delicious food and drinks while listening to live music and spending time with friends in the warm summer air.


June 5, 2022

Riverfest is an exciting day of live music, fun kids’ activities, shopping from local craftspeople, and delicious festival food. The day attracts residents who enjoy the gorgeous summer weather and a day of family-oriented fun.

Mashomack International Polo Challenge - June 18, 2022

June 18, 2022
Pine Plains

Enjoy the view of a thrilling polo game at the Mashomack International Polo Challenge, hosted by the Mashomack Polo Club. The day starts with a luncheon under tents and a champagne reception before the match begins. Afterward, watch talented players from around the world delve into the mounted game and cheer on your favorite team.

Hudson Valley Food Truck Festival - June 25, 2022

June 25, 2022

Dig into some of the best plates in the area at the Food Truck Festival. Enjoy all of the great activities at Barton Orchards in between bites from The Mac Factor, La Ruta Del Sol, Eddie’s Churro Factory, and more.

Rhinebeck Crafts Festival - June 25-26, 2022

June 25-26, 2022

See the finest work from local artisans at the Rhinebeck Crafts Festival. From fine art to clothes and home goods to jewelry, this is a great event to find unique gifts for friends and family members and some things for yourself. Local distilleries and wineries provide some refreshments, and restaurants will be offering gourmet treats. As you browse, catch some of the wandering entertainment — stiltwalkers, jugglers, and more.


Fourth Of July Celebration

July 4, 2022
Highland Falls

Celebrate America at the Fourth Of July Celebration in Highland Falls. The day starts with a parade and includes games, tasty food, icy drinks, and live music. Naturally, the grand finale is a spectacular fireworks show.

Pleasantville Music Festival

July 9, 2022

Attend one of Hudson Valley’s hottest music events, the Pleasantville Music Festival. See live performances from notable artists, including 10,000 Maniacs (“What’s The Matter Here”), Paula Cole (“I Don’t Wanna Wait”), and Battle of the Bands winner Carter Quinn Tanis (“See You In The Sun”). A beer and wine garden offers all your favorites, and some of the best local restaurants cater the event.

Pride In July at Barton Orchard

July 23, 2022
Get wild and support the LGBT community at Barton Orchard’s Pride In July. Compete in a drag show, see Tina Burner from Ru Paul’s Drag Race live, and enjoy live music. The night ends with a stunning fireworks show.


Sunflower Festival at Barton Orchards

August 5-14, 2022

Explore the five-acre field of sunflowers, pick your own fruits and vegetables, and go on a hayride at Barton Orchards’ Sunflower Festival. The petting zoo, crafts from local vendors, and delicious food available round out a day to close out the summer season in style.

Dutchess County Fair

August 23-28, 2022
Don’t miss the 176th year of the Dutchess County Fair. This event includes six days of indulgent fair foods, rides, games, and shows. Live performances at the Grandstand include ventriloquist/comedian Darci Lynne, country music stars Chris Jansen and Jimmie Allen, and American Idol winner Chayce Beckham. Other major attractions include the Horse Show, Century Museum Village, and the thrilling Rodeo.
Hudson Valley is no stranger to unique festivals and events. If you don’t already live in the area, contact Byron Anderson at HW Guernsey Realtors to see some of the Hudson Valley homes for sale.

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