An Insider’s Guide to May Events in the Hudson Valley

Local tourism directors share their top picks for things to do throughout the month.


Albany Tulip Festival

Photo by Discover Albany


We’ve said it before and we’ll say it again. There are a ton of things to do in the Hudson Valley each month. In fact, when it comes to actually choosing between one event or another, there’s potentially too much to do. Food fest on Saturday? Great. But there’s also that play you wanted to see. Oh, and that workshop you RSVP’d for in the afternoon. And the…oh wait, that’s already two things too many!

To help scout out the best events in the Valley, we reached out to local tourism directors from Albany to Ulster for their top picks for things to do. Check out their selections, then get planning!


Albany County

Discover Albany President and CEO Jill Delaney shares her top recommendations for the month:


Albany food tour

Historic Downtown Albany Food Tour / Photo by Discover Albany


Historic Downtown Albany Food Tour

Throughout Albany
Fridays, May to October

This May marks the return of the Historic Downtown Albany Food Tours, which run every Friday afternoon until October. Take a bite out of Albany as you explore the city on a unique, guided walking tour that spotlights historic facts, local landmarks, and, of course, the beverages and cuisine that make the Capital Region so scrumptious.


Albany History Fair and Living History Day

Throughout Albany
May 5

Take a trip back in time on May 5 with Historic Cherry’s Hill’s 20th Annual Albany History Fair and Ten Broeck Mansion’s Living History Day. At the fair, visitors can explore the literary history of the region as they listen to staged poetry readings and tour the historic libraries hidden within the city. At Living History Day, which is presented by the Albany County Historical Association, attendees can imagine the city during the Roaring ‘20s as they tour the Ten Broeck Mansion, listen to live music, watch historical re-enactors, and shop the wares from local vendors.


Albany tulip festival

Albany Tulip Festival / Photo by Discover Albany


Albany Tulip Festival

Washington Park, Albany
May 11-12

It’s back! Just in time for Mother’s Day, Albany’s signature Tulip Festival takes over the city. Beginning on Friday afternoon, the festivities commence with a traditional Dutch street scrubbing on State Street. Throughout the weekend, visitors and locals alike can make their way to Albany’s historic Washington Park for music, shopping from regional artisans, and tasty eats. Stay tuned for the crowning of the Tulip Queen and the announcement of the Mother of the Year Award. Just want to see the tulips? There will be more than 140,000 of the beautiful flowers to stop and smell and, you know, maybe take a selfie or two.


Moby Dick Book Club

Albany Pump Station, Albany
May 8, June 12, July 10, August 14, September 11

In honor of Herman Melville’s 200th birthday this year, Historic Albany Foundation, Discover Albany, and NYS Writers Institute host a monthly Moby Dick Book Club at the Albany Pump Station. Whether you’ve read the classic before or are finally brave enough to tackle the page-turner, you’ll love taking part in the community discussions over the course of six months. At each meeting, club members can chat with a Melville enthusiast, then participate in the Moby Dick programming for the evening.

Dutchess County

Take a peek at President & CEO of Dutchess Tourism, Inc. Mary Kay Vrba's top picks for things to do in Dutchess County this month:



11th Annual Millbrook Literary Festival

Millbrook Library, Millbrook
May 18, 10 a.m. – 5 p.m.

Calling all Hudson Valley bookworms! For the eleventh year, Millbrook’s literary festival takes over the town for a full day of reading books, talking about books, and celebrating the wonders of literature. The schedule is packed, so preview the program beforehand to pick and choose which workshops you’d like to attend. Whether you love to flip though comic books or page-turning novels, you’ll love the chance to surround yourself with talented authors and quality reads. Keep an eye out for Jennifer Castle, the voice behind American Girl’s special Hudson Valley doll, and Newberry Award-winning author Gail Carson Levine, to name only a few.


Memorial Day Weekend with FDR

Franklin D. Roosevelt National Historic Site, Hyde Park
May 25-27

Take a trip to FDR’s Hyde Park home on Memorial Day weekend for family fun in the great outdoors. Bring the kids for crafting, comedy, live music, jugglers, and more throughout the course of the three days. Before you leave, wander through the Field of Honor to see the hundreds of American flags on display to honor those who have served the nation and the community.



Our tickets for the Rhinebeck, New York are on available now. Click on link in bio. The Country living Fair is highly curated with the best of the best vendors which makes for a really enjoyable shopping experience because as you go from booth to booth you'll find not only find inspiration but also unique treasures to take home. // #rhinebeckny #dutchesscounty #clfrhinebeck #clfair #clfairfinds #countrylivingmag #interiordesign #farmhousedecor #farmhousestyle #artisan #art #maker #antique #vintage #gourmetfood #shabbychic #shoptillyoudrop #fashion #handmade #thrillofthehunt #repurposed #cookingdemo #homedecor #makersgonnamake #vintagedecor #farmhousechic

A post shared by Stella Show Mgmt. Co. (@stellashows) on


Country Living Fair

Dutchess County Fairgrounds, Rhinebeck​
May 31-June 2

Sneaking in at the tail end of May, Country Living’s multifaceted fair returns to the Dutchess Fairgrounds for crafting and shopping galore. Browse the wares from more than 200 vendors, who stock everything from antiques and homegoods to plants and vintage treasures. Each day, the fair welcomes special guests for live seminars, cooking demonstrations, and how-to instruction. Keep an eye out here to check which 2019 guests are confirmed.


Greene County

Read on for Tourism Director for Greene County Heather Bagshaw’s picks for things to do in May:



Rip Van Winkle Wine, Brew & Beverage Festival

Historic Catskill Point, Catskill
May 11

This May, the Fortnightly Club of Catskill hosts its 13th annual Rip Van Winkle Wine, Brew & Beverage Festival to celebrate the craft alcohol scene in Greene County. Come for the assortment of wineries, breweries, and distilleries, then stay for the picturesque views of the Hudson River from Historic Catskill Point. In addition to the top sips, attendees can also munch on local eats and sway to the live music that colors the fest throughout the day.


Hunter Mountain Film Festival

Hunter, Tannersville
May 16-18

For the first year ever, the Hunter Mountain Film Festival takes over the Doctorow Center for the Arts in Hunter and The Orpheum Film and Performing Arts Center in Tannersville to honor the upcoming filmmakers in the industry. Over the course of three days, the fest will host panels with top directors, producers, talent agents, and actors like Heidi Eklund (owner of Hudson Valley Casting), Hunter Emery (Orange Is the New Black), and Wayne Pyle (HBO’s Succession), to name only a few. The festivities conclude with the Gala Awards at the Hunter Mountain Ski Resort, which honors filmmakers for Best Feature and Short Films, Documentary, Web Series, and Student Films, along with Best Actor, Actress, and Director.


Greene County Driving Tour

Mountain Cloves Scenic Byway, Catskills

Make the most of spring weather In the Hudson Valley with a drive through the stunning Mountain Cloves Scenic Byway. The path bisects the Catskills, offering panoramic vistas that spotlight the crisp mountains, waterways, and farmland that live in harmony around it. If you’re in the mood for a day trip, pack a picnic basket for the drive and make a pitstop at a nearby park or preserve for a light lunch in the great outdoors.


Springtime Hiking

Catskill Park

There’s no hike like a spring hike in the Hudson Valley! The next time you need a reprieve from the workweek, take in a breath of fresh air during a restorative hike in Greene County’s Catskill Park. Whether you walk for 15 minutes or two hours, you’ll love the opportunity to connect with nature and let go of the little stresses of everyday life.

Orange County

Check out Orange County Tourism Director Amanda Dana’s selections for the best things to do this month.



Hudson River Cruises


Kick back and relax with a sightseeing cruise on one of the fine local liners that call the Hudson River home. Beginning on May 5, prospective riders can hop on The River Rose for day or evening cruises in the region. Two days earlier, on May 3, Pride of the Hudson kicks off its first sightseeing cruise of the season. Later in the month, it keeps the fun going with a Mother’s Day brunch cruise on May 12 and a murder mystery dinner cruise on May 18.


Derby Day

Goshen, Walden

Celebrate the Kentucky Derby in the Hudson Valley with two fun happenings in Orange County. In Goshen, the Historic Track hosts its Fifth Annual Kentucky Derby Day for locals who want to watch the big day on the big screen. Break out the fancy hats for the festive event, which also features lawn games like horseshoes, cornhole, racing, and more. In Walden, meanwhile, Angry Orchard brings the springtime fun with its Kentucky Derby Rose Club, which brings the spirit of the Southern derby to the cider garden. If you go, don’t forget to don your derby finest – we’re talking bowties, suspenders, and oversized hats – for top tunes, cider cocktails, and a chance to watch the race with friends.


Booze, Blues, and Beautiful Views

Throughout Orange County

With so many top-rated wineries, breweries, and distilleries in Orange County, it’s hardly a surprise that they’re some of the top spots to spend the day in spring. If wine is your thing, head to Brotherhood Winery on May 4 for its Death of a Gangster murder mystery dinner theater. At Palaia Winery, meanwhile, Jack Higgins and Friends bring rock and blues to the grounds on May 26. Also that weekend, Warwick Valley Winery and Distillery host a Bob Dylan Tribute Festival to kick off summer music season in the Hudson Valley.

For beer and cider lovers, we have something for you too! Hit Glenmere Brewing Company beginning on May 4 for its Bluegrass, Brews, and BBQ series, which runs every Sunday through October. At the weekend events, melodies by The Bunker Boys pair perfectly with finger-licking barbecue and Glenmere beer. Cider fans, on the other hand, should make a beeline to Angry Orchard for its ongoing Barrely Awake Tour or, on May 3, for the grand reopening of the orchard treehouse.


Outdoor Adventures

If you’re a nature aficionado in the Hudson Valley, Orange County is the place to be this spring. At Tuxedo’s Sterling Forest State Park, for instance, visitors can reach new heights – literally – on the Fire Tower Hike on May 11, which involves a four-mile loop to the Sterling Forest Fire Tower. For young adventurers, I Love My Park Day on May 4 and the Map & Compass Reading session on May 18 are a great way to teach little learners practical skills in the great outdoors.



A post shared by Cate Misczuk (@postcardsfromcate) on


Great Gatsby Gala

Foundry 42, Port Jervis
May 11, 7-10 p.m.

Break out your flapper finest for Foundry 42’s Great Gatsby Gala on May 11. The retro fest takes party-goers straight to the Roaring 20s with vintage tunes, old-school fashions, and dancing all night long. Giggle water flows at the cash bar, while a live jazz band and endless appetizers keep the good times going.

Rockland County

Browse through the top local things to do in Rockland County throughout the month of May:



Piermont Historical Society Swing Night

The View on the Hudson, Piermont
May 2, 6:30-10:30 p.m.

Step back in time to the 1900s for Piermont’s annual swing night. The fest hearkens back to the days when the riverside spot was a premier resort destination in the Hudson Valley. Throughout the festive evening, attendees can wine, dine, swing, and jive to the tunes of the Norm Hathaway Big Band. This event sold out a week in advance last year, so pick up your ticket early if you want to jazz it up in Piermont.


The Great Nyack House Tour – Architectural Gems

May 11, 10 a.m. – 4 p.m.

Now in its eighth occurrence, the Great Nyack House Tour spotlights the hidden gems of the Rockland region. Thanks to the Historical Society of the Nyacks, architecture enthusiasts can take in the stunning Gothic Revival and Queen Anne Victorian styles that color the area and serve as vivid reminders of the Valley’s rich history.


Live Art & Beer Fest

Garner Arts Center, Garnerville
May 18-19

It may be the first year for Live Art & Beer, or L.A.B., fest, but it already promises to be a repeat event in the region. After all, with 40 breweries, live performances, interactive installations, and art demonstrations, the two-day festival has more than enough to keep beer and art fans entertained all day long. Visit the site to see if your favorite local breweries are on the lineup, then score tickets to the exciting Hudson Valley event.



Don’t miss your last chance to see “Souvenir” this weekend @penguinreptheatre photos by @chrisyacphoto

A post shared by Penguin Rep Theatre (@penguinreptheatre) on


Art at Penguin Rep Theatre

Penguin Rep Theatre, Stony Point
May 17-June 9

Skip the movie theater and head to Stony Point’s Penguin Rep Theatre to see Art, the play by Yasmina Reza that explores the humor and tensions surrounding luxury and friendship. A winner of a Tony Award for Best Play and Olivier Award for Best Comedy, Art is a worthwhile way to spend an evening in the Hudson Valley.

Ulster County

Read up on Ulster County Tourism's event highlights for May:


Mohonk Preserve

Mohonk Preserve / Photo by Michael Bloom


Healthy Ulster County Week

Throughout Ulster County
May 3-12

Join Ulster County as it works to improve the overall health of local residents during this special themed week. Throughout the 10-day period, local businesses and groups offer signature promotions and programming to help interested individuals improve their eating and fitness habits and educate themselves about best health and wellness practices.


Woodstock Cycling Grand Prix

Women's Woodstock Cycling Grand Prix / Photo by Nin Lei Photography


Seventh Annual Women’s Woodstock Cycling Grand Prix

Rock City Rd, Woodstock
May 3-5

Over the course of three days, this women-only competition takes riders around Woodstock, Saugerties, Shandaken, and Hurley in an attempt to increase equality in the male-dominated sport. Beginning on Friday, the Grand Prix kicks off with a community dinner at Woodstock Fire Department. On Saturday, riders pedal to the metal during individual time trials and a circuit race, with a road race in Woodstock closing it all out on Sunday.


Community Day

Opus 40, Saugerties​
May 18, 10:30 a.m. – 5 p.m.

Mark your calendar for May 18, the day that Opus 40 in Saugerties invites the Hudson Valley community at large to make the most of a free visit to the scenic grounds. As you take in the stunning harmony of nature and art, don’t forget to take breaks to nod along to tunes by Max’s New Hat and rest your head during a chair massage from Woodstock Healing Arts. When the lunchtime munchies hit, ease the hunger pangs with farm-to-table eats from the Farmers & Chefs food truck, then wash it all down with a local brew from Dutch Ale House.



454 Washington Ave Extension, Saugerties​
May 22-September 8

HITS is back! Starting on May 22, Ulster County’s signature horseracing competition returns for a jampacked eight weeks of shows that dole out $3 million in prize money. The calendar commences with HITS-on-the-Hudson 1, which runs until May 26. If you’ve never spent the day at the picturesque racetrack before, make a point to watch the talented horses and their riders do their thing this May.

Related: Bookmark This Complete May Calendar of Events

Edit Module
Edit ModuleShow Tags
Edit Module
Edit Module