Events are in Full Bloom This May In Upstate NY!
- Hudson Valley Happenings
- May 1, 2025
- 14 min read
May Is Bringing the Heat — Are You Even Ready?!
This isn’t just a list, it’s your official permission slip to cancel your plans, rally your crew, and live your best spring life. From cherry blossom dreams to antique car heaven, cannabis cups to craft markets, epic concerts, castles, flower fields, fire arts, and fantasy realms — May in New York is stacked with jaw-dropping, memory-making, "I can’t believe we almost missed that!" kind of events.
Every single weekend has something wild, weird, beautiful, and fun waiting for you. So charge the phone, pack the snacks, and let this blog be your blueprint to an absolutely unforgettable month.
May 2 - 4
Lyndhurst Mansion
635 South Broadway
Tarrytown, NY
Kick off your May with a burst of creativity at the Spring Crafts at Lyndhurst, Artrider’s longest-running and most beloved craft festival. From May 2nd to 4th, the picturesque grounds of the Lyndhurst Mansion transform into a vibrant marketplace featuring over 200 of the nation’s finest artisans. Discover unique, handcrafted treasures perfect for Mother’s Day, graduations, weddings, or simply treating yourself. Stroll through booths brimming with original fashions, accessories, jewelry, home décor, and functional art in ceramics, glass, metal, wood, and more. With live craft demonstrations, interactive puppet theater, face painting, and storytelling, there’s entertainment for the entire family .
But the experience doesn’t stop at shopping. Savor gourmet foods, indulge in tastings from local distilleries and wineries, and enjoy a variety of culinary delights from food trucks offering BBQ, seafood, vegetarian options, and sweet treats like ice cream. After satisfying your taste buds, take a leisurely walk through Lyndhurst’s 67-acre estate, included with your craft show admission. Marvel at the breathtaking Hudson River views, explore the rose garden, and consider a tour of the magnificent Gothic Revival mansion for an additional fee . With free on-site parking and activities rain or shine, this event promises a delightful day out for all ages. Don’t miss this opportunity to immerse yourself in art, culture, and the beauty of spring. For tickets and more information, visit
May 2–4
Dutchess County Fairgrounds
6636 Route 9
Rhinebeck, NY
Start your engines—Rhinebeck’s legendary spring car show is back and bigger than ever. For over half a century, this three-day automotive extravaganza has drawn gearheads, collectors, and curious cruisers from all over the Northeast. The weekend kicks off Friday with the massive swap meet, where hundreds of vendors take over the fairgrounds with rare parts, vintage signage, tools, and all the chrome you can carry.
Saturday is the Rod & Custom Dust-Off, spotlighting hot rods, street rods, customs, race cars, and pickups—plus 30+ awards for standout builds. Sunday shifts gears to showcase unmodified antique and classic vehicles (pre-2000), judged across 60 classes with first, second, and third-place honors. The Car Corral is packed with rides for sale, and there’s free parking, paved walkways, and plenty of food to keep you fueled. Tickets are $18/day, with weekend passes available. Kids 12 and under get in free. This is the kind of event where history rumbles to life—and you don’t want to miss!
May 2–3
The Wire Event Center
60 South River Street
Coxsackie, NY
Get ready for a weekend celebrating the finest in New York's craft cannabis at the NY Small Farma Craft Flower Cup. Taking place on May 2nd and 3rd at The Wire Event Center in Coxsackie, this event brings together licensed growers, home cultivators, and cannabis enthusiasts for a unique competition and forum. Participants will showcase their best flower entries, judged by a panel of cultivation experts, budtenders, and consumers on criteria like aroma, taste, potency, and overall vibe. It's a chance to experience the pinnacle of small-batch, hand-crafted cannabis and connect with the community that makes it all possible.
It's not just about the competition, the event offers a vibrant farmers forum, providing insights into sustainable cultivation practices and the future of craft cannabis in New York. With vendor booths, networking opportunities, and educational sessions, attendees can immerse themselves in the culture and innovation driving the industry forward. Whether you're a seasoned grower or a curious newcomer, the Craft Flower Cup is the place to be for inspiration, education, and celebration. Don't miss this opportunity to be part of New York's growing cannabis movement.
May 3
1601 Route 9D
Garrison, NY
Spend your Saturday evening wrapped in sound and scenery at Boscobel House and Gardens for the Rising Artists Concert, a special one-night-only performance that brings the future stars of classical music center stage. Set on the historic bluff overlooking the Hudson River, this intimate open-air concert will feature four exceptionally gifted young musicians from the Chamber Music Society of Palm Beach’s prestigious Rising Artists program—each selected for their extraordinary talent and expressive artistry.
Under the direction of acclaimed violinist Arnaud Sussmann, the program weaves together a stunning mix of works, including Puccini’s emotionally rich “Crisantemi,” Shostakovich’s gripping String Quartet No. 8, and the lush, spirited beauty of Dvořák’s “American” Quartet. Guests are invited to arrive early to explore Boscobel’s blooming gardens and panoramic river views, then settle in as the music begins at golden hour. With the natural beauty of the Hudson Highlands as your backdrop and the raw talent of tomorrow’s great performers before you, this concert promises a soul-stirring experience you won’t soon forget.
May 3
Peekskill Riverfront Green Park
1 Robin Dr
Peekskill, NY
Spring is officially in bloom at the Peekskill Cherry Blossom Festival! On May 3, the Riverfront Green Park transforms into a sea of pink petals and pure good vibes, with 100+ blossoming cherry trees creating one of the dreamiest backdrops you’ll find anywhere along the Hudson. Hosted by the Rotary Club of Peekskill, this free, family-friendly festival packs a full day of live music, local food trucks, artisan vendors, and activities designed to celebrate community and the beauty of the season.
It’s not just about soaking up the views — there’s plenty to do, too. Stroll through the bustling plant sale to snag some gorgeous greenery just in time for Mother’s Day. Let the kids get creative with flowerpot painting, crafts, games, and inflatable fun. Pick up a few raffle tickets for a shot at cash prizes, with all proceeds supporting local and international Rotary service projects. Whether you’re coming for the flowers, the food, or just a beautiful riverside day, the Peekskill Cherry Blossom Festival is the perfect spring escape.
May 10–11
Washington Park
1 New Scotland Ave
Albany, NY
Albany bursts into bloom this Mother’s Day weekend as the 77th Annual Tulip Festival transforms Washington Park into a kaleidoscope of color. With over 140,000 tulips in 150 varieties, the park becomes a floral paradise, celebrating the city's rich Dutch heritage. From 11 AM to 6 PM on both days, enjoy live music across multiple stages, a fine arts show, and a bustling marketplace featuring local artisans and delicious food vendors. The festival kicks off with the traditional street scrubbing on May 9 and includes the Tulip Queen coronation and the Capital Region's Best Mom ceremony.
Families will find plenty to delight in, from the KidZone's interactive activities to wellness classes and workshops. Admission is free, and convenient parking with shuttle services is available from designated lots. Whether you're a local or a visitor, the Albany Tulip Festival offers a vibrant and memorable way to celebrate spring.
May 17 - 18
St. Mary’s Episcopal Church
1 Chestnut Street
Cold Spring, NY
Mark your calendars for a weekend of creativity and community at the Modern Makers Market in Cold Spring. On May 17th and 18th, the picturesque lawn of St. Mary’s Episcopal Church will host over 60 talented artisans and artists, showcasing a diverse array of handcrafted goods—from intricate jewelry and ceramics to bespoke textiles and fine art. This vibrant marketplace offers a unique opportunity to support local makers and find one-of-a-kind treasures.
But the experience doesn't stop at shopping. Enjoy live music performances that set the perfect backdrop for your day, and savor delicious offerings from a variety of food trucks. The event is dog-friendly, so feel free to bring your furry companions along. With free admission and a welcoming atmosphere, the Modern Makers Market promises a delightful experience for all ages. Conveniently located just a short walk from the Metro-North station, it's an easy day trip for city dwellers seeking a charming escape.
May 23–25
Corning’s Gaffer District
Market St
Corning, NY
Get fired up for one of the hottest Memorial Day Weekend events in the state—GlassFest is lighting up downtown Corning with three full days of live glassblowing, art, music, food, and serious small-town magic. Celebrating the city's legacy as the birthplace of American glass innovation, this festival brings together over 100 vendors, incredible public art, and hands-on experiences that let you watch—and feel—the fire arts in action. The streets of the Gaffer District transform into a massive block party where creativity pours from every corner.
But wait till the sun goes down. The Rock the Park concert series takes over Riverfront Centennial Park with free performances by national acts (hello, Vertical Horizon and Tony Jackson), and Saturday night ends with fireworks over the Chemung River. There’s a Kids Zone for the little ones, glassblowing demos by Corning Museum of Glass pros, and a Sunday Memorial Day Salute that brings the whole community together. Whether you're looking to shop, dance, eat, or just be dazzled—GlassFest delivers.
May 24–26
Ulster County Fairgrounds
249 Libertyville Road
New Paltz, NY
Celebrate Memorial Day weekend immersed in creativity at the Woodstock-New Paltz Art & Crafts Fair, a cherished tradition in the Hudson Valley since 1982. From May 24th to 26th, the Ulster County Fairgrounds will host over 200 juried artists and makers from across the nation, offering a diverse array of handcrafted treasures—from intricate jewelry and ceramics to bespoke furniture and fine art. Attendees can engage directly with artisans, witnessing live demonstrations and gaining insight into the craftsmanship behind each unique piece. The fair also features live music performances, including a set by HMHBand on May 24th, adding to the vibrant atmosphere.
Beyond the art, the fair is a feast for the senses. Savor gourmet specialties, sample local wines, spirits, and craft beers, and explore specialty foods and healthcare products. Families will appreciate the dedicated children's tent filled with activities to entertain younger visitors. With its scenic setting and rich offerings, the fair provides an ideal day out for all ages. Tickets are $12 for adults, $10 for seniors, and free for children, making it an accessible event for everyone. Don't miss this opportunity to support local artisans and experience the vibrant culture of the Hudson Valley.
May 23–25
Various Locations Along
NY Routes 28, 30 & 3
Adirondack Park, NY
Get ready to embark on a treasure-hunting adventure across the Adirondacks during Memorial Day Weekend! The Great Adirondack Garage Sale stretches over 200 miles, connecting communities like Old Forge, Inlet, Raquette Lake, Indian Lake, Blue Mountain Lake, Long Lake, Tupper Lake, Cranberry Lake, Piercefield, Newcomb, Speculator, and Piseco. With hundreds of garage sales along NY Routes 28, 30, and 3, you'll find everything from vintage antiques and rustic furniture to handcrafted goods and unique collectibles.
This annual event is more than just a series of yard sales—it's a regional celebration of community spirit and the joy of discovery. Whether you're a seasoned bargain hunter or a casual browser, there's something for everyone. Plan your route, explore charming towns, and uncover hidden gems along the way. For maps, listings, and more information, visit greatadirondackgaragesale.com.
May 24
Bethel Woods Center
200 Hurd Road
Bethel, NY
Dave Matthews Band is bringing their legendary live energy to Bethel Woods, and it’s going to be a night to remember. On May 24, the iconic band returns to one of the most historic concert grounds in the country—yes, that Woodstock. Whether you’ve seen them a dozen times or this is your first DMB experience, prepare to be swept away by their genre-blending sound, insane musicianship, and feel-it-in-your-soul vibes.
Want to make a weekend of it? You can! Bethel Woods is offering onsite camping for both tents and RVs, so you can roll in, rock out, and crash under the stars—no long drive home needed. With the gates opening at 5:30 PM and the show kicking off at 7:30 PM, it’s the perfect chance to soak in the music, the mountains, and the magic of a truly unforgettable night. Tickets are moving fast—grab yours and start planning the ultimate Memorial Day weekend escape.
May 24–26
Friends of the Walkway's
Victor C. Waryas Park
3 Main St
Poughkeepsie, NY
Kick off your summer season riverside at Mayfest, one of the Hudson Valley’s most anticipated Memorial Day weekend events! Hosted by Friends of the Walkway, this three-day celebration is bursting with everything we love about this region: hyper-local food and drink, handcrafted goods, live music, and serious community spirit. With over 190 vendors setting up shop along the banks of the Hudson River, you’ll find everything from fresh produce and small-batch sauces to handmade jewelry, soaps, woodwork, home goods, and more.
And let’s talk tastings—your $5 admission gets you samples from 30+ regional wineries, breweries, distilleries, and cideries, so you can sip your way through the best beverages in the Valley. (Pro tip: Walkway Over the Hudson members and kids under 12 get in free.) Add in nonstop live music, art installations, interactive kids' activities, character meet-and-greets, and food trucks slinging everything from tacos to vegan delights—and you’ve got yourself a full-day hang. It's pet-friendly, family-friendly, and 100% good vibes. Mayfest is more than just a market—it’s a celebration of what makes the Hudson Valley shine.
May 24–25
428 Route 216
Stormville, NY
Get ready to dive into a treasure trove of vintage delights at the Stormville Airport Antique Show & Flea Market! Celebrating over 55 years of flea market magic, this iconic event transforms the Stormville Airport into a bustling marketplace with over 400 vendors from across the region. Whether you're a seasoned collector or a casual browser, you'll find everything from antique furniture and rare collectibles to handcrafted goods and unique finds that you didn't know you needed.
As featured on HGTV's "Flea Market Flip," Stormville is more than just a market—it's an experience. Wander through aisles of eclectic stalls, savor delicious bites from local food trucks, and soak in the vibrant atmosphere that keeps visitors coming back year after year. With free admission and parking, it's the perfect weekend outing for families, friends, and treasure hunters alike. Just remember: it's rain or shine, and while the deals are hot, pets need to stay at home.
May 24–25
Columbia County Fairgrounds
182 Hudson Avenue
Chatham, NY
Raise a glass to the flavors of the Hudson Valley and the Berkshires at the Hudson Berkshire Wine & Food Festival, returning Memorial Day weekend for its annual celebration of regional craftsmanship. On May 24 and 25, the Columbia County Fairgrounds will host an impressive lineup of award-winning wineries, distilleries, cideries, and craft breweries, all offering unlimited tastings with your souvenir glass. Explore a vibrant marketplace featuring local artisans, gourmet food producers, and specialty vendors showcasing everything from cheeses and baked goods to jams and maple syrups.
The festival isn't just for adults—families are welcome to enjoy live music, free face painting, and special attractions like Rhonda’s Reptiles on Saturday and the 4 J’s Petting Zoo on Sunday. Food trucks and concessions will be on-site to satisfy every craving, and the event is held rain or shine, with indoor vendor spaces ensuring a comfortable experience. Children 12 and under are admitted free, and a portion of ticket sales will support local EMS services through the Columbia County Rotary Clubs. Whether you're a seasoned connoisseur or a curious newcomer, this festival offers a delightful weekend of sipping, savoring, and supporting local businesses.
May 29
Bethel Woods Center
200 Hurd Road
Bethel, NY
Country megastar Luke Bryan is bringing his high-octane "Country Song Came On Tour" to the legendary Bethel Woods Center for the Arts on May 29. Set on the historic grounds of the 1969 Woodstock festival, this venue offers a unique blend of rich musical heritage and modern amenities. Joining Luke are special guests George Birge, Avery Anna, Drake Milligan, and DJ Rock, promising a night filled with unforgettable performances. With gates opening at 5:30 PM and the show starting at 7:00 PM, attendees can look forward to an evening of chart-topping hits and country charm.
Enhance your concert experience with premium options like reserved lawn seating, access to the Green Room lounge, and exclusive box seat bundles. For those seeking a full weekend getaway, consider camping on-site to fully immerse yourself in the festival atmosphere. Whether you're a longtime fan or new to his music, this concert promises an unforgettable experience. Tickets are available now—secure your spot today and be part of a night that celebrates music, community, and the enduring legacy of live performance.
May 31–June 1
Dutchess County Fairgrounds
6636 Spring Brook Ave
Rhinebeck, NY
Step into a world of creativity and craftsmanship at the Rhinebeck Crafts Festival, returning to the scenic Dutchess County Fairgrounds on May 31 and June 1, 2025. This vibrant event brings together over 165 of the nation's finest artisans, offering a curated selection of handmade treasures you won't find anywhere else in upstate New York. From original fashions and accessories to exquisite jewelry, home décor, and fine art, the festival is a haven for those seeking unique, handcrafted items. Enjoy live craft demonstrations, interactive family activities, and a chance to meet the talented makers behind the creations.
While enjoying this incredible shopping experience, indulge in gourmet specialties and tastings from local distilleries and wineries, savoring the flavors of the Hudson Valley. With a variety of food options, including crepes, comfort food, Mexican cuisine, and classic festival favorites like hamburgers and ice cream, there's something to satisfy every palate. After exploring the festival, take advantage of Rhinebeck's charming offerings—dine at award-winning farm-to-table restaurants, visit historic estates, or enjoy breathtaking views on the Walkway Over the Hudson. The festival runs rain or shine, with indoor and outdoor booths, free parking, and a family-friendly atmosphere.
May 28 – June 1
Turning Stone Resort Casino
5218 Patrick Rd
Verona, NY
Elvis may have left the building, but the spirit of Lake George’s legendary Elvis Festival lives on in epic fashion. The event has been reimagined as the Empire State Tribute Festival, now calling the Turning Stone Resort Casino its new home—but don’t worry, it still brings the rhinestones, swiveling hips, and heart-thumping classics fans have come to love. Over five dazzling days, some of the top Elvis Tribute Artists in the world compete, perform, and channel The King with uncanny precision and jaw-dropping showmanship.
Expect big stage energy with themed concerts, competitions, Vegas-style glitz, and plenty of hip-shaking fun in one of Upstate New York’s most iconic entertainment venues. Whether you're a lifelong Elvis fan or just down for a wild weekend of music, sequins, and nostalgia, the Empire State Tribute Festival is your chance to relive the golden era—one jumpsuit at a time. Long live the King!
May 29 – June 1
1 Downtown Ithaca Commons & Stewart Park
Ithaca, NY
Kick off your summer with the Ithaca Festival, a four-day celebration of art, music, and community that has been a beloved tradition since 1977. From May 29 to June 1, downtown Ithaca transforms into a vibrant hub of creativity, featuring over 70 live performances, a bustling craft fair, and a variety of family-friendly activities.
The festivities begin with the iconic parade on Thursday evening, setting the tone for a weekend filled with local talent and artistic expression. Explore nearly 100 vendor booths offering unique handmade goods, from jewelry and pottery to artisanal foods and beverages. Enjoy performances across multiple stages, showcasing a diverse lineup of musicians and entertainers. Families can delight in interactive art workshops and activities designed for all ages. With its inclusive atmosphere and free admission, the Ithaca Festival is the perfect way to experience the heart and soul of this dynamic community.
May 31–June 8
Camp Herrlich
5 Wilbur Herrlich Rd
Patterson, NY
Grab your cloak, sharpen your wit, and prepare to step straight into a living storybook at Kingdom Faire! This isn’t just another renaissance festival — it’s an all-out medieval fantasy experience where the world you know disappears and a world of knights, rogues, pirates, and magic takes over. Set across lush, rolling grounds, the day unfolds with live, immersive performances where you're not just watching the story—you’re in it. Every hour brings a new twist, a new quest, and new characters to meet.
As you wander the kingdom, shop hand-forged weapons, intricate jewelry, mystical potions, and one-of-a-kind artisan crafts. Refuel with hearty eats and raise a mug of ale at the Fan & Dagger Pub (trust us, you’ll want to linger). There’s archery, games, epic photo ops, and plenty of surprises that’ll have you laughing, cheering, and maybe even swearing loyalty to a new cause. Whether you come in costume or just bring your imagination, Kingdom Faire is pure magic for anyone ready to leave the real world behind—even if just for a day.
May 24 – October 26
New York Botanical Garden
2900 Southern Blvd
Bronx, NY
Step into a living masterpiece at the New York Botanical Garden's "Van Gogh’s Flowers," opening May 24. This immersive exhibition brings the vibrant blooms of Vincent van Gogh's paintings to life, transforming the garden into a canvas of sunflowers, irises, and other floral inspirations. Wander through stunning horticultural displays that mirror Van Gogh's iconic works, offering a multisensory experience that blends art and nature in perfect harmony.
Beyond the breathtaking gardens, the exhibition features rare artworks, interactive installations, and engaging programs that delve into Van Gogh's artistic journey and his profound connection to the natural world. Whether you're an art enthusiast, a nature lover, or simply seeking a unique spring outing, "Van Gogh’s Flowers" promises an unforgettable experience that celebrates the beauty of both art and flora.
And there you have it — May, is absolutely crushing it.
From the first flower bloom to the final firework, this month is bursting with reasons to get out there and make memories. Whether you're dancing under the stars, filling your bags with handmade finds, or road-tripping for the perfect antique score, New York is serving it all up on a silver platter.
So go chase the magic, the music, the mayhem — and don’t forget to tag us @hudsonvalleyhappenings when you do. We’ll see you out there, spring adventurers.
We'll See You Amongst the Flowers!
HVH Team
