Warmer days are back again! Spring into Dutchess County by following our guide of the best May events the area has to offer. Stroll, sip, shop, and soak up spring across the Hudson Valley with charming markets, garden tours, live music, artisan workshops, and feel-good events perfect for gathering with friends and family.
Rhinebeck Antique Car Show and Swap Meet
May 1-3
Dutchess County Fairgrounds, Rhinebeck
The car show will feature hot rods, street rods, customs, race cars, and compact customs/pickups. On Sunday, many great antique and classic cars are parked in 60 classes.
rhinebeckcarshow.net
Aglaia Jewelry Pop-up Opening
Friday, May 1
Irwin Garden, Rhinebeck
Shop a beautiful collection of Aglaïa Jewelry pieces at Irwin Garden. Celebrate the arrival of Spring with flowers, jewelry, drinks and bites.
aglaiajewelry.com
Tivoli First Fridays
Friday, May 1
Town of Tivoli
Tivoli’s First Fridays are back! Enjoy open houses and warm welcomes–stroll, sip, shop, and art hop through Tivoli, and stick around for live music in the village.
tivolinow.com
Cheese 101 – Sheep and Goat’s Milk
Friday, May 1
Beacon Cheese Shop, Beacon
Join the Beacon Cheese Shop for Cheese 101, a guided tasting class where they’ll explore the unique and delicious world of sheep and goat milk cheeses.
thecheeseshops.com
Contemporary Series – “On the Edge” by Greenroom Ensemble
Saturday, May 2
Chelsea Morrison Theater, Millbrook School, Millbrook
This program traces a wide arc of chamber music, and moves through a series of bold, contemporary works that reimagine how sound, rhythm, and ensemble interaction can unfold.
millbrookmusicsalon.org
3rd Annual Angry Orchard Cider Tasting Festival
Saturday, May 2
Angry Orchard Cider House, Walden
Join Treasury Cider and many other New York State cideries at Angry Orchard for their 3rd annual Cider Tasting Festival. There will be live music, lawn games, cider tastings and food for purchase.
fishkillfarms.com
Silk Scarf Workshop at Clover Brooke Farm
Saturday, May 2
Clover Brooke Farm, Hyde Park
Unlock the beauty of nature’s palette in this unique introductory natural dyeing workshop at Clover Brooke Farm. This workshop will guide you through the fascinating art of eco-printing, where flowers, leaves, and food waste transform fabric into vibrant, wearable works of art.
cloverbrookefarm.com
A Run to Remember – 5k/10k Farm Trail Run and Walk
Saturday, May 2
Greig Farm Trails, Red Hook
Join in a community run or walk to honor loved ones lost. Support each other and enjoy some sunshine at the farm. Afterwards, grab a bite from the Greig Farm Cafe.
thegreigfarm.com
Open Daffodil Viewing
Saturday, May 2
Innisfree Garden, Millbrook
Each spring, Innisfree bursts into color as thousands of heirloom daffodils bloom across the landscape.
innisfreegarden.org
Isadora at Flora’s Feast: Heaven in a Wildflower
Saturday, May 2
VBI Theater, Poughkeepsie
The Isadora Duncan International Institute premieres Isadora at Flora’s Feast: Heaven in a Wildflower at the Cunneen-Hackett Arts Center VBI Theater. The evening burgeons onstage through original and new choreography and videography shaped by garden paths and the cyclical flowering of life itself.
Buy Tickets
The Artist Film Screening
Saturday, May 2
The Stissing Center for Arts & Culture, Pine Plains
Witness a true classic film–in the 1920s, Jean Dujardin is a bona fide matinee idol with many adoring fans. George finds himself falling in love with an ingenue named Peppy Miller and it seems Peppy feels the same way, but George is reluctant to cheat on his wife.
thestissingcenter.org
Lotus Lantern Craft Workshop
Saturday, May 2
Millbrook Library, Millbrook
Join the Korean Spirit and Culture Promotion Project for a hands-on workshop where you’ll create a beautiful lotus flower lantern using colored paper and a pre-made wireframe.
Register now!
Mother’s Day Tea Party
Saturday, May 2
Bangallworks, Stanfordville
Stanford Recreation invites you to join them at Bangallworks for a Mother’s Day Tea Party, with light refreshments and a guided tea sampling from Harney & Sons. This is a free event, registration is required.
stanfordny.myrec.com
Spring Market
Sunday, May 3
Lasting Joy Brewery, Tivoli
Enjoy some lovely spring shopping at Lasting Joy Brewery’s Spring Market, happening rain or shine. Shop local vendors and enjoy food, drinks, and live music.
lastingjoybrewery.com
Apple Blossom Festival
Sunday, May 3
Fishkill Farms, Hopewell Junction
Celebrate all things spring at Fishkill Farm’s Apple Blossom Festival and Vendor Market! There will be food trucks, sweets, live music, wagon rides, and more.
fishkillfarms.com
“Gilded Age Scandals” Tour
Saturday, May 9
Staatsburg State Historic Site, Staatsburg
Led by a costumed guide, learn about the scandalous behavior and intrigues of the very rich during this 90-minute tour of the mansion.
Reservations required!
Garden Matters: Roots to Blooms with Kristen Essig
Saturday, May 9
Stonewood Farm, Millbrook
Explore the value of utilizing plants in their entirety, from underground roots to blossoms and seeds. Examine how whole-plant practices reduce waste, support healthier soils, more resilient farms, and more equitable food systems.
stonewoodny.org
“Daisies for Daisy” Paint and Sip
Saturday, May 9
Wilderstein Historic Site, Rhinebeck
Unleash the artist within at this acrylic painting workshop led by Risa Getman. Paint and take home a still life of a lovely bouquet of daisies. Learn how to prepare your canvas, layering, shading, and more. Wine, nibbles, and materials all included.
wilderstein.org
Tablao Flamenco
Saturday, May 9
The Stissing Center for Arts & Culture, Pine Plains
Tablao Flamenco transforms the theater into a warm, intimate Andalusian-style nightclub. World-class singers deliver voices filled with joy, longing, and grit, while virtuosic guitarists lay down intricate rhythms.
thestissingcenter.org
Apple Blossom Day
Saturday, May 9
Red Hook Rotary Club, Red Hook
This festival celebrates the arrival of spring with a variety of activities, including live music, entertainment, food vendors, and opportunities to shop for Mother’s Day gifts.
redhookrotaryclub.com
Beer, Burgers, and Bourbon Party
Saturday, May 9
Taconic Distillery, Standfordville
Kick off the spring season and warmer weather at the tasting room on the patio of Taconic Distillery! Enjoy live music, a build-your-own-burger station, Vosburgh Brewing beers, and cocktails.
taconicdistillery.com
Mother’s Day Brunch
Sunday, May 10
The Grove Restaurant & Bar, Red Hook
Treat the mother(s) in your life to a delicious meal at The Grove; enjoy a special a la carte menu featuring fresh lobster and refreshing drinks.
thegroveatredhook.com
Mother’s Day 2026
Sunday, May 10
Troutbeck, Amenia
Treat mom to a special prix fixe menu at Troutbeck that highlights spring ingredient stars, such as ramps, asparagus, fava beans, and english peas.
troutbeck.com
Annual Mother’s Day Plant Sale
Sunday, Monday 10
Vitsky Bakery, Wassaic
Join Vitsky Bakery for their third annual Mother’s Day plant sale. Thistle Pass Farm and Foxtrot Farm & Flowers will be on the Vitsky patio with all the veggie and flower garden starts you could ever want.
thistlepass.com
Mother’s Day Curator’s Tour
Sunday, May 10
Innisfree Garden, Millbrook
Take the mother(s) in your life on a beautiful garden tour led by landscape curator Kate Kerin. A lively tour exploring Innisfree, a quintessential American stroll garden.
innisfreegarden.org
Wassaic Project Summer Exhibition; Opening Reception
Saturday, May 16
Wassaic Project, Maxon Mills, Wassaic
Join the Wassaic Project for a grand opening of their newest exhibition, on view all summer – Because, now is the time of monsters. Featuring 39 artists with works focusing on the space between a dying world, and one not yet known.
wassaicproject.org
Velvet Confessional: An Intimate Vaudeville
Saturday, May 16
Savage Wonder, Beacon
Enjoy a preshow performance of torch singers, food, drinks, and dancing. Then, stick around for a theatrical show of five short plays with singers, dancers, mimes, and other acts in between.
Get tickets!
Meet the Director Behind Bathing Beauty
Saturday, May 16
The Moviehouse, Millerton
Director Brian Gerston will join us for a discussion and Q&A after a screening of his documentary film about Hollywood’s most glamorous swimming star – Hollywood’s Mermaid: The Esther Williams Story, and a screening of her 1944 classic Bathing Beauty.
themoviehouse.com
Dahlia Daze: Dahlia Tuber Festival
May 16-17
Foxtrot Farm & Flowers, Stanfordville
Get ready to stock your garden straight from the source! Browse an incredible variety of tubers, swap knowledge with the experts, and connect with the fellow dahlia-obsessed.
foxtrotfarmflowers.com
Tea Time and Alpacas
Sunday, May 17
Clover Brooke Farm, Hyde Park
Sip locally sourced tea, and indulge in handcrafted sweets shaped like llamas and alpacas, all while these gentle animals graze peacefully nearby.
cloverbrookefarm.com
Mediterranean Cuisine Boot Camp at the CIA
May 18–22
The Culinary Institute of America, Hyde Park
With its emphasis on healthful ingredients and vivid flavors, Mediterranean cooking has become a favorite among Americans. In this boot camp, you’ll utilize the unique pantries and flavor profiles of diverse regions.
register.culinary.edu
Throwback Party at the Four Brothers Drive-In
Thursday, May 21
Four Brothers Drive-In Theater, Amenia
Join the Four Brothers Drive-In for their first throwback party of the season, in collaboration with Boondocks Film Society! Special showing of the original Josie and the Pussycats, with live music and pre-show entertainment, film-inspired cocktails and food, and more!
playeatdrink.com
Stormville Airport Antique Show and Flea Market
May 23-24
Stormville Airport Flea Market, Stormville
At this local antique show favorite, hundreds of vendors offering antiques, jewelry, furniture, artwork, collectibles, crafts, new and vintage clothes, and so much more. Food and drink vendors on-site as well.
stormvilleairportfleamarkets.com
Memorial Day BBQ 2026
Saturday, May 23
Troutbeck, Amenia
Troutbeck’s lauded culinary team will prepare a festive spread sourced from local farms, celebrating the unofficial start of summer! Music, lawn games and early summer fun abound.
troutbeck.com
Farm Yoga
Saturday, May 23
Fishkill Farms, Hopewell Junction
Set on their covered, wraparound porch, enjoy a serene practice overlooking blooming flower gardens, rolling orchards, and scenic mountain views.
fishkillfarms.com
Community Open-Air Concert
Sunday, May 24
Bennett Park, Millbrook
In collaboration with Millbrook Arts Group, an open-air Concert Truck by Chinese pianist Susan Zhang and Artistic Director Sophia Zhou perform in Bennett Park—bring your picnic blanket, family, and snacks.
millbrookmusicsalon.org
Memorial Day Sunset Flag Changing Ceremony
Sunday, May 24
Center Overlook of Walkway Over the Hudson, Poughkeepsie
Join veterans affairs and VFW members for a sunset ceremony that includes a four-gun salute, the playing of Taps, local artists performing God Bless America, and a carnation toss into the Hudson River.
walkway.org
Memorial Day Celebration
Monday, May 25
Brexel-Schlathaus Park, Wappingers Falls
The Town of Wappingers invites you to attend their annual Memorial Day Ceremony at Brexel-Schlathaus Park located at the corner of All Angels Hill and Myers Corners roads. The ceremony will start at 2:00 pm.
More Info!
Town of Hyde Park Memorial Day Parade
Monday, May 25
Hyde Park Drive-In, Hyde Park
Watch marchers, floats, cars, firetrucks, and bands as they line up and march down Route 9 to honor America’s heroic veterans. Everyone is encouraged to attend Memorial Services by the American Legion at the town hall afterwards.
More info!
Baking with Cheese at the Beacon Cheese Shop
Tuesday, May 26
Beacon Cheese Shop, Beacon
Join the Beacon Cheese Shop for a hands-on Baking with Cheese class. In this fun, delicious class you’ll bake three different recipes—a mix of savory and sweet—all showcasing the magic of specialty cheese in the kitchen.
thecheeseshops.com
Community Concert– “Compass: Musical Distance”
Friday, May 29
Lyall Community Church, Millbrook
This program centers on Da Lontano—music shaped by distance, direction, and memory—anchored by a unique collaboration between clarinetist Graeme Johnson and the multi-awarded Balourdet Quartet.
millbrookmusicsalon.org
Opening Day at Wethersfield Estate & Garden
Friday, May 29
Wethersfield Estate & Garden, Amenia
Opening with expanded offerings, including additional house and carriage house tour dates. Discover the finest classical Italian garden in the United States.
wethersfield.org
High Horse Performance
Friday, May 29
The Stissing Center for Arts & Culture, Pine Plains
Four friends, three bows, and one pick: High Horse is a progressive acoustic string band (fiddle, guitar/banjo, cello, and bass), blending Bluegrass, Old-Time, and Celtic influences with the energy of alternative rock.
thestissingcenter.org
The Bang Group Performance
Saturday, May 30
The Stissing Center for Arts & Culture, Pine Plains
New York City’s The Bang Group, directed by choreographer David Parker and dancer Jeffrey Kazin, returns to Stissing Center with A Mouthful of Shoes, a dynamic suite of rhythm-driven dances.
thestissingcenter.org
Llamaste Yoga and Lavender Loofahs
Sunday, May 31
Clover Brooke Farm, Hyde Park
Join Clover Brooke Farm for a fun session of Yoga, alongside fluffy, friendly llamas with yoga instructor Virginia Bocchicchio. Followed by a hands-on class creating your own lavender loofah.
cloverbrookefarm.com
Hudson Valley Free Day at Dia:Beacon
Sunday, May 31
Dia:Beacon, Beacon
Hudson Valley residents receive free admission to Dia Beacon on the last Sunday of each month. Explore beautiful works of art by well-known and newfound artists, in a gorgeous indoor and outdoor atmosphere.
diaart.org