Embrace the magic of late summer with Dutchess County’s August calendar, overflowing with festivals, fresh flavors, live entertainment, scenic escapes, family traditions, and memorable moments under sunny skies.
Summer Cider Party
August 1–2
Fishkill Farms, Hopewell Junction
Soak up the summer with a cider-inspired party at Fishkill Farms, hosted by Treasury Cider. Enjoy handcrafted hard cider, live music, food trucks, cider donuts, and a pick-your-own bouquet of flowers to take home.
treasurycider.com
Mid-Hudson Comic Con
August 1–2
MJN Convention Center, Poughkeepsie
The Hudson Valley’s premier pop culture celebration. This high-energy, family-friendly 2 day event showcases the best of comics, anime, gaming, and fandom.
mjncenter.org
Great Estates Garden & Landscape Weekend
August 1–2
Participating Locations: Wilderstein Historic Site, Staatsburgh State Historic Site, Mount Gulian Historic Site, Beatrix Farrand Garden at Bellefield, Vanderbilt Mansion, Clermont State Historic Site, Innisfree Garden
Explore some of the most beautiful gardens and landscapes in Dutchess County. Visit on your own or a part of a guided tour during this weekend celebrating the county’s more historic and gorgeous estates.
Hudson Valley Caribbean Festival
Saturday, August 1
Waryas Park, Poughkeepsie
A celebration uniting the community through Caribbean culture, heritage, food, and entertainment.
hudsonvalleycaribbeanfestival.com
Flower Hammering Workshop
Sunday, August 2
Staatsburgh State Historic Site, Staatsburgh
Practice the art of flower pounding and make beautiful, botanical prints on greeting cards. Materials and instruction included, light refreshments served.
eventbrite.com
Special Screening & Director Q&A
Thursday, August 6
Four Brothers Drive-In, Amenia
Enjoy a special screening of Over Your Dead Body, with a Q&A from the film’s director, Jorma Taccone. Enjoy live music, preshow entertainment, film-inspired foods, and specialty cocktails.
playeatdrink.com
Trivia on the Pavilion
Thursday, August 6
Terrapin Restaurant, Rhinebeck
Enjoy a fun and lively night of “Trivia with Andre.” Get there hungry, thirsty, and ready to play; full food and drink menu available.
terrapinrestaurant.com
Nature-Inspired Art
Friday, August 7
Innisfree Garden, Millbrook
Participants will make art inspired by the natural world, including trail bracelets, bark and leaf rubbings, nature wall hangings, and clay impressions using leaves, seeds, bark, and other natural materials.
Summer Children’s Series: “The Myth of Persephone”
Saturday, August 8
The Stissing Center for Arts & Culture, Pine Plains
Through masks, music, and storytelling, children help rescue Persephone while discovering the ancient story behind the changing seasons – a celebration of creativity, environmental awareness, and the joy of performance.
thestissingcenter.org
Jazz in the Vineyard
Saturday, August 8
Millbrook Vineyards & Winery, Millbrook
Enjoy an open-air concert by Mary Ann Palermo & the First Take Band right on the beautiful vineyard lawn of the Millbrook Winery. Food trucks on site.
millbrookwine.com/jazzconcerts
Yoga at Clermont
Sunday, August 9
Clermont State Historic Site, Germantown
Join instructor Jai Sugrim for a morning of relaxing yoga at Clermont; bring your own yoga mat and get ready to stretch, breathe, and be at peace.
friendsofclermont.com
Eastdale Second Fridays
Friday, August 14
Eastdale Village, Cottage Square, Poughkeepsie
Enjoy live music, special shop offerings, and delicious bites from one of Eastdale’s bistros. Shop, eat, dance!
eastdalevillage.com
Stony Kill Butterflies & Booms Festival
August 9–16
Stony Kill Farm, Wappingers Falls
A week-long festival celebrating the beauty and ecology of the local pollinators. Enjoy amazing lectures, and live music, hayrides, activities, face painting, crafts, and food trucks at the festival finale.
stonykill.org
Bouquet & Brush: Painting Class
Saturday, August 15
Fishkill Farms, Hopewell Junction
Join Samantha B. for a relaxing and creative afternoon at Fishkill Farms. Create your own bouquet arrangement using a selection of fresh summer flowers that Samantha provides, and follow step-by-step instructions as you paint your floral design on canvas.
treasurycider.com
Beacon Sloop Club Corn Festival
Sunday, August 16
Pete & Toshi Riverfront Park, Beacon
Free admission for all, fresh lemonades, chilled watermelon treats, and of course, all things corn! Enjoy butter corn-based snacks all day long and live music.
beaconsloopclub.org
Open Mic Night
Friday, August 21
Stissing Center for Arts & Culture, Pine Plains
A welcoming evening for music, spoken word, comedy, and every kind of self-expression. Artists of all ages and experience levels are invited to share.
thestissingcenter.org
Nature Scavenger Hunt
Innisfree Garden, Millbrook
Friday, August 21
Young explorers will search for colors, textures, water, rocks, living things, garden structures, and other discoveries throughout the garden. At the end of the hunt, participants can return to the starting point to receive an Innisfree Explorer prize pack.
Walkway At Night
Friday, August 21
Walkway East (Poughkeepsie) and West (Highland) Entrances
From 212 feet above the river, take in breathtaking views as the moon rises overhead and the lights of Poughkeepsie and Highland shimmer in the distance.
walkway.org
Open Mic and Food Truck Night
Friday, August 21
Treasury Cider Porch, Hopewell Junction
Musicians of any experience level are welcome to share their talents in a relaxed and supportive setting. Enjoy hard cider and delicious food from From the Grounds Up food truck.
treasurycider.com
Haven Heritage Equestrian Trail Ride
Friday, August 21
Winley Farm, Millbrook
Join trainer Danielle Sagliano for a guided trail ride through the grounds of Winley Farm. Enjoy scenic trails, countryside views, and a charcuterie board and wine pairing at the end.
Reserve a spot with: havenheritageequestrian@gmail.com
Summer Children’s Series: “Monster Intelligence”
Saturday, August 22
Stissing Center for Arts & Culture, Pine Plains
Filled with colorful characters and original songs spanning rock, jazz, pop, and Broadway, this family-friendly musical celebrates different ways of learning and encourages kids to discover their own “monster intelligence.”
thestissingcenter.org
Family Fun Weekend at Barton Orchards
August 22–23
Barton Orchards, Poughquag
Enjoy live music, children’s entertainment, magic shows, delicious food, and a petting zoo. For the adults, there’s hard cider at one of three bars on site.
bartonorchards.com
8th Annual Sunflower Festival
August 28–30
Barton Orchards, Poughquag
Live music, hard ciders, delicious food, and a gorgeous field of late-summer sunflowers. Walk the grounds, visit the petting zoo, and take in all the family-fun you can.
bartonorchards.com
2026 Dutchess County Fair
August 25–30
Dutchess County Fairgrounds, Rhinebeck
Dutchess’ favorite summer tradition is back for its 180th year. Food, games, petting zoos, rides, live music, craft vendors, and so much more.
dutchessfair.com
2026 Annual Festival at Kaatsbaan
Saturday, August 29
Kaatsbaan Cultural Park, Tivoli
A festival of community and storytelling, with amazing live performances, music, and dance.
kaatsbaan.org
