Events & Activities In The Catskills & Hudson Valley | April & May 2026
Posted by Coldwell Banker Village Green Realty on Tuesday, April 14th, 2026 at 10:50am
It’s spring 2026 in the Hudson Valley and Catskills, and the events that are available across the Upstate region are as eclectic as all get out! From puppets to alpacas, from hardcore backpacking to relaxing retreats, from plays about artistic differences between a country mouse and a city mouse to hunts for tadpoles, if you want to take a break from work (please take a break from work) and enjoy yourself, there are so many options that aren’t just something to do for a few hours, but something to remember for a long time.
As the top-selling real estate company in the region* we stay as plugged into what’s available for our clients and neighbors in learning and leisure in each of the towns we live and work in. Here are our picks for April and May, chosen largely for their uniqueness and local connections. Enjoy your time off, Upstaters!
Catskill Mountain Shakespeare’s Production of Hamlet
Where: Hudson Valley, NY
Catskill Mountain Shakespeare is known for their energetic, creative staging of the best of The Bard. This year, they’re taking their production of Hamlet on tour throughout the Catskills community – Phoenicia Playhouse, Opus 40, The Catskill Mountain Foundation – they’ll be performing at 9 different spots through April and May. We’re calling out May 3rd’s performance at Van Dusen’s in Lexington as the one to try if you’re available. Why? We love the concept of Van Dusen’s. It’s part country store, part bar, part performance space. It’s set in one of the prettiest towns in the Catskills, and they’re covering the bases for that small village that needs covering – non-ironic finger snaps for them. Everyone has a take/gimmick when staging Hamlet. What’s Catskill Mountain Shakespeare’s bent? They’re setting it amidst the 80s punk scene and whittling it down to 90 minutes (bravo!). Go, take a hike before, enjoy Lexington’s scenery, and be able to say you saw some good Shakespeare!
Aaron Foster at the Woodstock Guild
Where: Woodstock, NY
One-time HGTV star Aaron Foster has turned comedian to rave reviews. “It’s mostly jokes… mostly. Growing up with a bipolar father and a schizophrenic older brother left Aaron Foster with a combination of survivor’s guilt, depression, and anxiety that has invalidated his every accomplishment, destroyed his every relationship, and invaded his every waking thought. A comedy!” Laugh at him, maybe at yourself, and maybe at the people you share The Woodstock Guild’s intimate performance space with.
Ashtray - The International Museum of Dinnerware Design
Where: Kingston, NY
There are many museums across the Hudson Valley and Catskills region, but the IMoDD holds a special place in our hearts. So much of what we think of as “home” is centered around our tables and meals. This museum celebrates the dinnerware that makes our meals - from the fabulous to the purely functional. Their current exhibit’s name is self-explanatory. It’s also a walk down memory lane. Ashtrays, which were once ubiquitous, have more or less disappeared from our everyday (yes, almost none of us miss the second-hand smoke – but don’t you miss those elementary school pottery projects?) Visit for a reminder of a more analog time.
Trail Running Film Festival @ Denizen Theatre
Where: New Paltz, NY
We love it when events are really niche. Want to meet new people? Show up to a deeply niche event that’s outside your usual niches! This festival will screen seven films from across the globe that center around trail running! Interesting people will show up!
East Durham Irish Festival
Where: East Durham, NY
May 22–24, 2026 at the Michael J. Quill Irish Cultural & Sports Centre in East Durham, NY, hosts one of the longest-running Irish festivals in the United States. Whether or not you come from an Irish heritage, there are entertainments to enjoy - music, dancing, food!
Bring-A-Friend Sound Bath - Divine Flow Boutique
Where: East Durham, NY
If you’ve never taken a sound bath, they make you feel incredible – sound waves flow through your body to the marrow, which, when done right, begins to feel like a life-giving jelly. Why wouldn’t you want your buddies to join you for this? When you reserve a spot for this sound bath, you can bring a friend. Receive forty-five minutes of soothing vibrations from crystal singing bowls, chimes, and other therapeutic instruments.
Bakersfield Mist
Where: Bridge Street Theatre, Catskill, NY
“Bakersfield Mist is a hilarious and thought-provoking comedy-drama that pits small-town smarts vs big city credentials in a battle over art and authenticity.” A play tailor-made for the “Upstate drama.”
Two Events From Assembly
One of Assembly’s great gifts to the Upstate scene is the variety of its programming. These two events couldn’t be more different, and they’re just wonderful drops in the bucket that is the May and June programming at Assembly.
Ecstatic Dance With Joro-Boro
Where: Kingston, NY
What starts with a composed warm-up and ends with a healing sound meditation has a center of pure ecstatic joy, movement, and community. Start your Sunday in an extraordinary way!
Knorrwood
Where: Kingston, NY
Ok! There are capes, elf ears, wizard hats, and weapons. There’s glitter, storytelling, and there are some very decent Led Zeppelin covers. This. Looks. Strangely. Awesome. Go because you can’t stay away, go on a dare, go because you need something wild and weird to do for a bachelorette party. We think it will be some great fun.
The Trailbound Project Catskill Backpack
Where: Windham, NY
The Trailbound Project is an NJ-based group that offers outings and classes in hiking. This is their first offering in a four-part Catskills series. It’s a weekend spent tenting and summiting Windham High Peak, Blackhead, Black Dome, and Thomas Cole. This one’s not for the inexperienced - you’re expected to have skills to grow on as you hike. But if you’re having trouble getting your friends on board for a multi-day hike, this is your opportunity to do it without going it alone! Join this small group and challenge yourself.
Kingston Independent Comic Expo
Where: Kingston, NY
Comic lovers, artists, self-publishers, zine makers – this event is for you! Events are split between The Old Dutch Church and St. James Church and include talks, workshops, panels, and seventy exhibitors of comics.
Spring Hiking Retreat in The Catskills
Where: Jewett, NY
Saturday, April 25th – This is a day that includes meditation and breathwork, a feast, a hike, and vegan dessert. This is a lovely day.
The Ashokan Center’s Ukulele Weekend
Where: Olivebridge, NY
The grounds of the Ashokan Center are beautiful. The all-weekend celebration of our favorite four-stringed instrument is the main draw, but Woodstock and the Reservoir are just a short drive away for those who need a breather. Whether you’ve been playing the ukulele for years or are brand-new, you’re invited to grow your skills, join the camper cabaret, and participate in all the classes and workshops.
Vernal Pool Ecology With Frank Parisio
Where: Rock Oak Preserve, West Hurley, NY
The Woodstock Land Conservancy offers some exploration of vernal pools every spring. What’s a vernal pool? Small wetland pools and puddles that support life in the early spring, and disappear as things heat up. Join naturalist Frank Parisio for a close look at the small wonders that sprout in these pools.
Hudson Valley Ideas Festival
Where: Rosendale Theatre, Rosendale, NY
This third annual festival is subtitled Staying Human. Thought leaders, entrepreneurs, and artists come together to discuss topics like AI in higher education, comedy, creativity and computers, and curing brainrot. Let’s get in a room and talk this out!
Midnight Rambles
Where: Levon Helm Studio, Woodstock, NY
It’s that time of year again. For 20 years, Midnight Rambles have paid tribute to Rock n' Roll and created a community among musicians. This is a quintessential Woodstock experience. The tickets go quite quickly, so click if you don't want to wait until next time.
Bearsville Bluegrass Festival
Where: Woodstock, NY
This one-day festival makes incredible use of the Bearsville Center property. There’s live Bluegrass, plenty of great food, lawn games, nature walks, a Rock N' Roll tour, and a unique community singing workshop. Bring your lawn chairs and plan to hang out for the entire day. Phoenicia Flea will be there if you need a side of local maker goodness with your Bluegrass fun.
Bite The Bullet: 18th Century Medicine
Where: Hudson River Maritime Museum, Kingston, NY
We don’t know if this opportunity will ever come around again. This is a lecture that explores the Revolutionary era medicine practiced by both trained and untrained physicians and traveling midwives. It’s bound to be full of facts you didn’t have in your arsenal before, and will perhaps answer the question, “How accurate are the medical treatments on Outlander?” History buffs and Jamie and Claire fans, you'll want to block off the afternoon of April 25th.
Mario The Maker Magician
Where: Woodstock Playhouse, Woodstock, NY
This is a great one for the kids – take them to a live performance, they’ll enjoy it while pulling them away from KPop Demon Hunters! You don’t need to hear those songs again! Mario comes highly recommended by David Blaine, who calls him "the BEST kids magician in the world!!" The contagiously upbeat Mario has also been dubbed "magic's punk rock Peter Pan philosopher.” We can’t quite picture that, but he’s been featured on The Tonight Show with Jimmy Fallon and Sesame Street, and now he’ll be in Woodstock. Again, we say, why not?
Field + Supply Spring Market
Where: Hutton Brickyards Kingston, NY
We’re not sure that Field + Supply needs any introduction or explanation anymore. It has become such a fixture of the Upstate scene. If you’ve never been before, it’s a weekend filled with the most beautifully made goods you can imagine, music, food, and hanging out on the Hudson. Heads up – pay attention to the parking options so that you don’t have to deal with circling full parking lots.
Discovering Place at CPW’s Community Gallery
Where: Kingston, NY
The Center for Photography Woodstock (now in Kingston) has a new gallery for local works. This exhibition is the culmination of the work of a group of six young artists taking a gap year with a fellowship through Place Corps Kingston. They’ve spent six months using photography to capture relationships, neighborhoods, and the everyday moments we have. Go to CPW to see this, as well as the additional works on display.
Mini Golf In The Stacks
Where: Elting Memorial Library, New Paltz, NY
So, at this event, put together by local teens, kids can play mini-golf amid the library’s shelves. The course winds through the stacks, and each hole is dedicated to a different fairy tale. We love it!
Legally Blonde @ SUNY New Paltz
Where: New Paltz, NY
If any movie ever begged to be made into a big, pink musical, it was Legally Blonde. Everyone will be bending and snapping at SUNY New Paltz. You should join them for a fun night at the theater.
Make Your Own Loofah At Clover Brook Farm
Where: Hyde Park, NY
Ahhh, Cloverbrook Farm, where the sheep and Alpaca roam, and they have some of the coolest, low-key workshops in the Hudson Valley. They offer classes on brewing beer and needle felting as well as a number of other farm-fresh activities. This loofah workshop is a good way to spend a Saturday afternoon and a great excuse to visit the animals.
Nerd Nite – A Talk on Poison and A Screening Of The Princess Bride @ Industrial Arts Brewing Co
Where: Beacon, NY
If loving The Princess Bride makes us nerds, give us the t-shirt. Nerd Nite puts together events that are “nerdy” and feature beer. Good combo. PBS host Trace Dominguez will be there to talk about poison (we’re hoping he stops short of providing pointers), and The Princess Bride will be just as good as you remember… just, “as you wish.”
Season Opening Scramble
Where: Inness, Accord, NY
This member’s event invites participants of all ages to tee off with a team, select the best shot, and take the next shot from there. Get a ringer on your team, and you could complete the course in record time and be the first to the BBQ.
Making Natural Watercolor Paints
Where: Hudson Valley Seed Company, Accord, NY
Rocks and minerals from our landscape become watercolors. Grind, mix, paint, and pick up your seeds, which are packaged in the Hudson Valley Seed Company’s famously beautiful seed packets!
Contact Improv Sundays @ Wildheart
Where: Wallkill, NY
Dancers – this one’s for you. Visit Wildheart, where they “support a spiral of cultural, embodied, creatively expressed love” at their land-based retreat in Wallkill for contact improv twice a month. If you want to dance in a beautiful, inspiring place, this is a low-cost, low-barrier way to do it. If you love it there, you can apply for an artist’s residency.
Landscapes and Life: Three Artistic Visions @ Tivoli Artists Gallery
Where: Tivoli, NY
Three local artists who frequently paint together come together to exhibit simple scenes from life. Tivoli is famed for its dining scene, so take in some art and grab a bite.
Creative Crit at Cone Zone Ceramics Studio
Where: Catskill, NY
Not just for ceramic artists, this monthly gathering offers creatives the chance to come together, present projects, get constructive feedback, work on grant proposals, and be with other creatives. Bring your writing, fine arts, and questions.
Paper Bead Bracelet Workshop at The Livingston Manor Library
Where: Livingston Manor, NY
When was the last time you saw one of these bracelets!!? If you’ve never made them before, they’re both engrossing to work on and easy. The kids will love spending some time at the library, and this is perfect timing to create something meaningful to give a mom or a grandmother on Mother’s Day.
Hudson Valley Puppet Slam
Where: Stissing Center, Pine Plains, NY
The Hudson Valley is packed with puppeteers! The Puppet Slam brings together a totally diverse group of artists whose common thread is puppets. “It’s a reflection of the Valley itself: creative, curious, generous, and unafraid to try something new, inviting audiences to see puppetry as both playful and deeply expressive.” A lot is going on April 25th, but this might be the event you’ll remember forever because…puppets!
What We Do With The Dead
Where: Park Theater, Hudson, NY
Park Theater Hudson has a romantic and ongoing renovation story you can read about here and here. It’s a story of caring for a historic building that needs a lot of love that we love. Despite the overall project that will bring the full building back to life not being quite complete, Park Theater Hudson has some incredible, eclectic programming in the portion of the building that has been painstakingly, beautifully restored. A special collaboration with Tectonic Theater Project brings What We Do With The Dead, which explores grief, friendship, and the experimentation of a writer who wants to say something that’s both true and funny, to the stage. Stephen Belber (Laramie Project, The Madness, Tape, Match) reads his solo work for two nights in April.
Buffalo Stack
Where: Park Theater, Hudson, NY
We mentioned the eclectic programming at Park Theater. The weekend after What We Do With The Dead, the space will host Buffalo Stack – they’re a Hudson Valley band with songwriter, guitarist, and vocalist Andy Stack at the helm. We think they’re the perfect Friday night band that has a dash of this, a dash of that, and not too much of anything.
A final suggestion: take a few minutes to browse around the sites of all the organizations that are hosting these events. We’ve mentioned just one or two of their theatrical, musical, crafty, gastronomic, and thought-provoking offerings here, but combined, they have hundreds more! Upstate living is the best!
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