Longer days and sunny skies have finally arrived! Welcome early summer in Dutchess County with a month of festivals, garden strolls, outdoor concerts, local flavors, and community celebrations. From scenic landscapes to lively Main Streets, June is the perfect time to get outside, reconnect, and make the most of the Hudson Valley’s sun-soaked days and warmer nights.
Birding Bonanza
Thursday, June 4
Wilderstein Historic Site, Rhinebeck
A birding expedition led by Alan Peterson of the Ralph T. Waterman Bird Club, and a walking tour of Wilderstein’s renowned landscapes. Wear your hiking boots and bring your binoculars.
wilderstein.org
Willy Porter at the Stissing Center
Friday, June 5
The Stissing Center for Arts & Culture, Pine Plains
A solo show with Willy Porter that is part concert, part conversation, part gentle reckoning—music as ritual, humor as grace, and connection as the point.
thestissingcenter.org
Foxtrot Fridays with Westerly Canteen
Friday, June 5
Foxtrot Farm & Flowers, Standfordville
Enjoy this monthly community gathering! Foxtrot will be host to local food, drinks, and live music! The flower shop will be open late!
foxtrotfarmflowers.com
Poughkeepsie Greek Festival
June 5–7
The Hellenic Center, Poughkeepsie
Hosted by the Kimisis Greek Orthodox Church, discover the delicious Mediterranean cuisine of the Greeks.
poughkeepsiegreekfestival.com
Rooted: A Seasonal Mind-Body Retreat Series
Saturday, June 6
Plan Bee Farm Brewery, Poughkeepsie
Yoga, acupressure, and Ayurvedic seasonal teachings. End the day with a tasting of Plan Bee’s locally sourced beers while learning about the brewery’s dedication to New York-grown ingredients.
herenowretreats.com
Great Estates Garden and Landscape Walk
Saturday, June 6
Wilderstein Historic Site, Rhinebeck
Enjoy a special tour of Wilderstein’s gardens and landscape, the exterior design of the mansion and outbuildings, and the lives of the Suckley family.
wilderstein.org
Help a Horse Day – 9th Annual Event
Saturday, June 6
13 Hands Equine Rescue, Clinton Corners
Meet rescued horses, donkeys, mules, and even zebras. Enjoy live music, food, local vendors, and demonstrations throughout the day. The event raises essential support for the year‑round care of 100+ rescued equines.
13handsequine.com
Looking at Nature: Bald Eagle Walk and Talk
Saturday, June 6
Innisfree Garden, Millbrook
An engaging walk-and-talk focused on one of Innisfree’s most popular resident species: bald eagles. Catch a glimpse of the nesting pair and, if you’re lucky, their young.
innisfreegarden.org
Beacon’s 5th Annual Food Crawl
Saturday, June 6
Main Street, Beacon
Beacon’s annual food festival is back for another year, celebrating all the delicious food Main Street in Beacon has to offer. Enjoy bites, drinks, and plenty of shopping.
thebeaconbeaconny.com
Rhinebeck Crafts Festival
June 6–7
Dutchess County Fairgrounds, Rhinebeck
Enjoy the Hudson Valley’s most unique shopping event! Shop clothing, jewelry, furniture, and fine art. Afterwards, grab a bite to eat at some of Rhinebeck’s best farm-to-table restaurants.
rhinebeckcraftsfestival.com
Stanford Pride
Saturday, June 6
Bangallworks, Stanfordville
Join the “loudest, out-est, proudest Pride that Stanford has ever seen!” Free for all, sponsored by the Stanford Pride committee and supporters. Enjoy food, drinks, dancing, and celebrations.
stanfordnypride.org
2026 Summer Benefit
Saturday, June 6
Maxon Mills, Wassaic Project, Wassaic
Join The Wassaic Project in celebrating their accomplishments over the past year while looking forward to what’s to come: seven-floor exhibitions, 100+ artist residencies, and new initiatives. Tickets include an open bar with beer, wine, cocktails, and hors d’oeuvres.
wassaicproject.org
Big Band Night
Sunday, June 7
Boscobel House and Gardens, Garrison
Bring a picnic dinner, enjoy the iconic view, and celebrate an early summer evening with music and dancing. The Big Band Sound jazz orchestra recreates the swinging sounds of the big band era and beyond.
boscobel.org
Plein Aire Workshop
Thursday, June 11
Wethersfield Estate and Gardens, Amenia
A hands-on workshop to learn the basics of plein aire painting–the practice of painting outdoors in the natural landscape. All art supplies will be provided.
wethersfield.org
Beacon LitFest Spring Festival
June 12–14
Main Street, Beacon
A three-day literary festival at multiple Beacon locations, now in its sixth year, featuring multi-award-winning authors including Julia Phillips, Alexander Chee, and Wayne Koestenbaum. Readings, workshops, and live performances.
beaconlitfest.org
Aim for Gold
Saturday, June 13
Mashomack Polo Club, Pine Plains
Aim for Gold is a fundraising event to directly benefit USA Archery and champion Team USA’s journey to the LA 2028 Olympic Games. This day-long celebration combines competitive fun with Olympic flair and family-friendly entertainment.
Get tickets!
Pawling Triathlon
Saturday, June 13
Lakeside Park, Pawling
The race is on, rain or shine! All age groups welcome to compete, free finish line photos, and a post-race snack and beverage station.
Sign up!
Taste of Millbrook 2026
Saturday, June 13
Millbrook Winery, Millbrook
Local flavors, great company, and every ticket directly funds the grants, instruments, programs, and “Bright Ideas” that have been shaping Millbrook’s next generation since 2001.
millbrookwine.com
Stissing Center 2nd Annual Art Auction
Saturday, June 13
The Stissing Center for Arts & Culture, Pine Plains
The Stissing Center and Mad Rose Gallery are set to host the second annual Art Auction. Browse and bid on exceptional artwork while supporting Stissing Center’s mission to bring people together through the shared experience of arts and culture.
thestissingcenter.org
Festival at the Falls – 10th Anniversary Celebration
Saturday, June 13
Mesier Park and Main Street, Wappingers Falls Village
Celebrating 10 years of bringing the village of Wappingers Falls together for a day filled with energy, creativity, and community spirit. Enjoy live music, historic tours, games, food, and sidewalk sales.
wfbpa.org
Tyte Gallery Opening Reception: In Plain Sight: The Luminous Plein Air Landscape
Saturday, June 13
Tyte Gallery, Millbrook
This traditional landscape exhibition showcases the on-site paintings of three of the Hudson Valley’s most noted artists who continue a tradition of working directly from nature in all types of conditions.
tytegallery.com
RevCon 2026—Revolutionary War History Fair
Saturday, June 13
FDR Presidential Library Lawn, Hyde Park
Hosted by Destination Dutchess at the FDR Presidential Library and Museum in Hyde Park. Cannon and musket demonstrations, living history exhibitions, and lectures on the Hudson Valley’s role in the Revolution. Free and family-friendly, part of the county’s Rev250 commemoration.
fdrlibrary.org
Poughkeepsie Pride March & Festival
Saturday, June 13
Victor C. Waryas Park, Poughkeepsie
The 8th annual event, free and family-friendly, begins with a march down Main Street and ends with a festival at Waryas Park on the Hudson. Dozens of vendors, food trucks, and community organizations.
dutchesspride.org
Beacon Sloop Club Strawberry Festival
Sunday, June 14
Pete and Toshi Seeger Riverfront Park, Beacon
Family activities and of course, strawberries! Enjoy fresh strawberry shortcakes, strawberry smoothies, chocolate-covered strawberries, and dozens of craft vendors selling handmade goods.
beaconsloopclub.org
Pawling’s 16th Annual Car Show
Sunday, June 14
Charles Coleman Blvd, Pawling
Pawling’s huge annual car show, right in the village. Live music, street vendors, local shops, food vendors, and a beer garden on site.
pawlingchamberofcommerce.com
Summer Sundays Block Party
Sunday, June 14
King’s Court Brewing, Cannon St, Poughkeepsie
Fun, family-friendly, and free admission for all! Enjoy food trucks, live music, games, crafts, beers, wine, ciders, and more!
kingscourtbrewingcompany.com
Saints & Sinners: 8th Annual Summer Solstice Festival
Friday, June 19
Prophecy Hall, Beacon
Moon, Serpent & Bone: Oddities and Curiosities Night Market, presents a night of ritual, fire, and presence. Witness fire, a saints and sinners performance, and a seance, with live music beforehand.
moonserpentandbone.com
Wappingers Historical Society Cocktail Gala
Friday, June 19
Historic Wappingers Falls Boathouse, Wappingers Falls
Honoring Rosemary and Denny Evaul and Dani Masterson for their longtime contributions to the Wappinger community. Enjoy hot and cold hors d’oeuvres and drinks, and live music.
wappingershistoricalsociety.org
A Day of Dance with Pilobolus at Innisfree
Saturday, June 20
Innisfree Garden, Millbrook
Innisfree will welcome Pilobolus for ‘A Day of Dance,’ a day of outdoor movement workshops on the garden’s scenic overlook. This program brings together Pilobolus’ inventive, collaborative approach to movement with one of the Hudson Valley’s most distinctive public gardens.
innisfreegarden.org
The 27th Mashomack International Polo Challenge
Saturday, June 20
Mashomack Polo Club, Pine Plains
This elegant afternoon of polo is the perfect way to kick off summer in style, right on the stunning grounds of Mashomack Polo. Alongside the polo action, all guests can enjoy light bites, an open bar, and shopping in the boutiques.
mashomackpolo.com
Strawberries and Acrylics–Painting Workshop
Saturday, June 20
Fishkill Farms, Hopewell Junction
Enjoy a two-hour guided class creating a beautiful berry-themed painting while you overlook the strawberry fields below. Sip on Fishkill Farms’ tree-to-bottle hard cider while you paint.
fishkillfarms.com
The Beatles, Elvis, and Beyond
Saturday, June 20
Marriott Pavilion at The Culinary Institute of America, Hyde Park
Celebrate some of the best years of music with a tribute concert by the Northern Dutchess Symphony Orchestra; featuring music from The Beatles, Elvis, Simon and Garfunkel, Brazilian Jazz, and more.
ndsorchestra.org
Summer Solstice: Sunrise to Sunset
Sunday, June 21
Innisfree Garden, Millbrook
Celebrate the longest day of the year from sunrise to sunset at Innisfree Garden. Experience the changing light throughout the day, nature-themed scavenger hunts, and beautiful garden tours.
innisfreegarden.org
Community Supper Club
Wednesday, June 24
Bennett Room, Millbrook Library, Millbrook
Join Chef Lenny for a potluck supper. Bring something to share, or just bring yourself and enjoy a meal in the company of friends and neighbors. May’s theme is I Was Drinking That. Bring any dish made with a beverage as an ingredient (cola, coffee, tea, juice, etc.) or a complimentary side or beverage.
More info!
Art Exhibit, Opening Reception: “Echoes in the Margin” By Delano Dunn
Thursday, June 25
Troutbeck, Amenia
The exhibition continues an ongoing collaboration between Wassaic Project and Troutbeck, rooted in a shared commitment to supporting artists, fostering public engagement, and advancing cultural exchange in the Hudson Valley. In “Echoes in the Margin”, Delano Dunn reimagines how Black identity and desire have been shaped and seen, and what it might look like to see them anew.
troutbeck.com
Upstate Art Weekend
June 25–29
Participating Counties in the Hudson Valley and Catskills
UAW’s flagship annual event brings together artists and audiences across the Hudson Valley and Catskills, inviting exploration of exhibitions, programs, and cultural spaces throughout the region.
upstateartweekend.org
Animals After Hours
Friday, June 26
Trevor-Lovejoy Zoo, Millbrook School, Millbrook
Spend an after-hours evening at the Trevor-Lovejoy zoo to discover all the interesting creatures that Millbrook School staff and students care for and research. BBQ food truck on site to serve up a tasty dinner.
millbrook.org/trevor-zoo
Trail Magic Day
Saturday, June 27
Native Landscapes and Garden Center, Pawling
Enjoy lawn games, delicious barbecue foods, and chats with hikers as they tell stories about their Appalachian Trail adventures.
pawlingchamberofcommerce.com
The Dances of Chihuahua
Saturday, June 27
The Stissing Center for Arts & Culture, Pine Plains
The Dances of Chihuahua invites children into an interactive workshop exploring the vibrant cultural dances of the Mexican region. Young participants will experience authentic movement while learning about Mexican culture and geography.
thestissingcenter.org
