Top 10 Events in Dutchess this Summer

Date Published: June 18, 2019

1. Rhinebeck Crafts Festival – June 22-23, 2019: Enjoy a day at the Dutchess County Fairgrounds with the whole family! Shop 200 of America's best independent artists and craftspeople, offering unique handmade goods, along with speciality food items, loca wines and spirits, kids entertainment and more! Visit the website for more details. 

2. Bard SummerScape - June 29-August 10, 2019: The 16th annual Bard SummerScape festival features seven weeks of world-class opera, theater, dance, cabaret, film, and music, including the 30th annual Bard Music Festival, Korngold and His World.

3. Bike New York Discover Hudson Valley Bike Ride – June 30, 2019: Centered around the Walkway Over the Hudson, the world’s longest pedestrian bridge, this ride is all about discovery. For some, that means taking it easy on one of the shorter routes and simply enjoying the gorgeous scenery. For others, it means discovering what you’re capable of—with more than 5,900 feet of climbing, the 100-mile route is a century worth bragging about. It’s not too late to register!

4. Hudson Valley Hot Air Balloon Festival – July 12-14, 2019: This annual event has become one of the most popular weekends for visitors to flock to the Dutchess County Fairgrounds in Rhinebeck, and for good reason. With sunrise and sunset photo ops as the balloons launch into the sky, it really is a sight to be seen! Balloonists will have room to launch and fly in all directions, enabling 360 degree views. Throughout the day enjoy vendors offering craft beverage tastings, specialty foods, helicopter rides, gifts and more! Learn more.

5. Dutchess Dragon Boat Race and Festival – July 20, 2019: The unique fiberglass boats are really something! Whether you’re participating, or cheering on along the banks of the Hudson River, this event is one to remember. While the races are going on, the shoreline will be humming with energy and excitement at the Riverside Festival. There will be a wide range of entertainment during the day, including food trucks, local community vendors, and artists! Get more info here.

6. Harlem Valley Rail Ride and Festival – July 28, 2019: If you enjoy biking and the outdoors you won’t want to miss one of the summer’s most beautiful rides! On July 28th, cruise through the gorgeous landscapes in Eastern Dutchess, ending in one of America’s coolest small towns, Millerton! Get registered for the ride today!

7. Jazz in the Valley Festival – August 18, 2019: This afternoon of music and art has grown into an annual festival, showcasing music performed by world-class musicians, fittingly complemented by breathtaking views of the Hudson River Valley as the backdrop from Waryas Park in Poughkeepsie. Get tickets!

8. Dutchess County Fair – August 20-25, 2019: Year after year the Dutchess County Fair returns to Rhinebeck and draws crowds of over 500,000 people, the second largest county fair in all of New York State. The fair continues to be a Dutchess County staple, and an event that attracts both locals and visitors alike. The list of vendors and attractions includes agriculture, horticulture, arts and crafts, antiques, crafts food and beverages, rides, live music and so much more! Start planning your trip to the Dutchess County Fair this August!

9. Hudson Valley Wine and Food Fest – September 7-8, 2019: A true celebration of culinary arts and craft beverages in the Hudson Valley, the fest features hundreds of wines from all over New York State and the world. In addition, taste more than 100 gourmet specialty goods, discover fine art and lifestyle vendors, and indulge in food sampling from some of the region's best restaurants. Purchase your tickets in advance and start planning your weekend in Dutchess!

10. Hudson River Craft Beer Festival – September 14, 2019: The 7th annual Hudson River Craft Beer Festival returns to Beacon this September for the biggest & best craft beer festival yet. Follow the river to Riverfront Park to sample over 180 craft beers from over 90 of America’s best craft breweries while enjoying live music, local vendors and delicious food. Tickets on sale now!