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Top 10 Events in August

Date Published: July 13, 2021

With the return of many signature Dutchess events, this month's Top 10 is one you won't want to miss! 


1. Frederick Douglass 1858 Speech Commemoration 

Sunday, August 1 at  2:00 p.m. at College Hill Park  

After portraying George Washington in the first national tour of Hamilton: An American Musical by Lin Manuel-Miranda, performer Paul Oakley Stovall developed an avid interest in the internationally recognized abolitionist leader Frederick Douglass. Stovall’s subsequent studies of Douglass have led him around the country and as far abroad as Ireland. On August 1, 2021, Celebrating the African Spirit will present the actor as he recites the Emancipation Day speech Douglass delivered to an audience of several thousand at Poughkeepsie’s College Hill Park in August of 1858. Stovall will return to that original site to perform the address at the pavilion atop the park. For more details click here


2. Millbrook Horse Trials

Thursday, August 5 to Sunday, August 8 at various times

The Millbrook Horse Trials is a recognized United States Eventing Association event and is an important part of a long equestrian tradition in Dutchess County. Recognized among the region's most prestigious annual sporting events, it attracts world-class competitors from throughout the United States and brings some 400 riders and their support staff into the local community each year. MHT is the largest event in the northeast and the only one with an advanced division. U.S Olympic team riders regularly compete for their upper-level horses at Millbrook to warm up for the top international competitions. Each day of the horse trials has a different flavor. Thursday and Friday are quieter days when you can enjoy the beautiful countryside, watch upper-level dressage, sample some delicious food from the food trucks and vendors, and shop at the Trade Fair. Saturday is much more lively with a country fair atmosphere! On Sunday, the upper-level show jumping is the climax of the competition! Patrons will enjoy lunch with their guests as they watch top-level riders compete in the finals from the comfort of their private ringside tents. For more details click here


3. Dutch's Spirits Gatsby Garden Party On the Great Lawn 

Saturday, August 14 from 12:00 p.m. to 9:00 p.m. at Dutch’s Spirits

Enjoy a night of Gatsby-inspired cocktails and dancing at Dutch’s Spirits which was built on the site of the largest bootlegging operation ever found in Dutchess County during prohibition. Enjoy bites of Oyster Party Brooklyn and Dutch’s own food truck, live jazz, a flower market pop-up, and a 1930s themed photo booth! Picnic tables are available, guests are welcome to bring their own chairs and blanket. Leashed four-legged friends are welcome! For details, click here


4. Jazz in the Valley

Sunday, August 15 at 12:00 p.m. at Waryas Park. Poughkeepsie 

Celebrate the future of jazz during the annual Jazz in the Valley concert. Claim your spot in their tent or bring your own chair, and join on the lawn which will have enhanced speakers for optimal enjoyment. The festival showcases music performed by world-class musicians, complemented by breathtaking views of the Hudson River Valley as its backdrop. This year’s line-up will include acclaimed tenor saxophonist Javon Jackson, Samara Joy, The Curtis Brothers, and more! For tickets and details click here.


5. Beacon Sloop Annual Corn Festival 

Sunday, August 15 from 12:00 p.m. to 5:00 p.m. at  Pete & Toshi Riverfront Park

Join the Beacon Sloop Club Annual Corn Festival featuring fresh-picked, ready-to-eat local‐grown sweet corn on the cob, watermelon, and other summer treats! Two solar power stages with live music. Many free children's activities, environmental displays, crafts, and food vendors. Fun for all ages! Sail the Hudson River and arrive at noon to sign up for free sails on the Woody Guthrie, weather permitting. For more details click here


​​6. Barton Orchards Cider Festival

Saturday, August 21 at Barton Orchards 

Take a trip to the farm during Hudson ValleyCiders, Seltzer & Sours Festival! This premium event will showcase over 40+ beverages to samples of local favorites and national brands.  Grab a bite to eat from one of the onsite food trucks and stop by Barton Orchards concession offering fresh-baked treats, ice cream. Bring your littles and visit the petting zoo, stroll through the PYO fields, and have a blast at their Fun Park, which is great for all ages. Hayrides and live music will be happening all day. For more details click here


7. 175th Annual Dutchess County Fair

Tuesday, August 24 - Sunday, August 29 from 10:00 a.m. to 10:00 p.m. at Dutchess County Fairgrounds

For six straight days, The Dutchess County Fair will celebrate agriculture in a way that individuals of all ages can enjoy! From livestock to local specialty foods and entertainment, it’s truly an experience for the whole family. As one of the finest carnivals in the entire country, this entertainment destination will feature Powers Great American Midways rides, Livestock, free shows, a vendor shopping center, and performances by Chayce Beckham, 2021 American Idol Winner, and Ian Flannigan, a finalist on NBC’s The Voice! Tickets will be sold online only. Please see details here

8. Wassaic Project Summer Block Party 

Saturday, August 28 from 4:00 p.m. to 10:00 p.m. at Maxon Mills 

Come party in Wassaic! This is the second of two block parties Wassaic Project is hosting in support of the 2021 Exhibition, If You Lived Here You’d Be Home By Now — featuring music, dance, film, activities for kids, and more. Plus, enjoy an artist talk with a Q&A portion. Get more details here


9. Tasting Menu at The Barns Art Center Opening Weekend 

Saturday, August 28- 29 11:00 - 4:00 PM at Barns Art Center

A treat for all five senses, The Barns Art Center presents Tasting Menu, an exploration of food as a metaphor, material, and meaning, through painting, photography, sculpture, and film. Join the celebration of contemporary art, community, and of course, food. Free and open to the public! For more details, click here


10. Pick-Own-Sunflowers in Dutchess

Various dates in August at Hudson Valley Cold Press Oils & Barton Orchards Farm 

Stroll through a field of fresh sunflowers at Hudson Valley Cold Pressed Oils! Pick your own sunflowers from their 10-acre field then take the perfect photo op at sunset. The tentative opening date is August 11. Please check their website for the most up-to-date information. Continue the PYO trail at Barton Orchards and join their Sunflower Festival happening two weekends in August. Once you’ve picked your favorite sunflower, have a bite, enjoy music, food and of course take in the beauty of the farm!

*Bonus Event: Kaatsbaan Cultural Park Summer Festival

August 28-29, September 4-5 & 11-12 at Kaatban Cultural Park 

Kaatsbaan Cultural Park will present a Summer Festival over three consecutive weekends, beginning August 28 and running through September 12, 2021, taking place both outdoors across its 153-acres in the Hudson Valley as well as in its indoor Theater. The multi-disciplinary festival will feature three new classical dance works with live music; a free weekend of western swing music, art, and picnicking; a film screening in partnership with the Woodstock Film Festival; and an inaugural outdoor end of summer dinner celebration. For more details, click here

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