Spring is in full swing across the Hudson Valley, and this week’s lineup is packed with something for everyone—from Mother’s Day celebrations and outdoor festivals to live music, markets, and community events. Whether you’re planning a family outing, a relaxed day exploring local art and farms, or a night out with friends, there are plenty of ways to enjoy the season.
You’ll find a great mix of free events, senior‑friendly activities, and social gatherings for young adults, making it easy to connect, explore, and take advantage of the warmer weather. With events happening throughout Westchester, Putnam, Dutchess, Rockland, and Orange County, it’s the perfect time to get out and experience everything the Hudson Valley has to offer this week.
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Westchester County Events
STEM‑tastic Festival (FREE / Family / Young Adults) — Rye — May 8
The Moth: Live Storytelling (Young Adults / Adults) — Tarrytown Music Hall — May 8
Hudson River Spring Festival (FREE / Family / Seniors) — Ossining — May 9–10
Yonkers Cinco de Mayo Parade & Festival (FREE / Family / Young Adults) — Yonkers — May 9
Mother’s Day Pop‑Up Market (FREE / All ages) — Yonkers — May 9
Ben Folds Concert (Young Adults / Adults) — Peekskill — May 9
Victorian Springtime Tours (Senior‑friendly / Historical) — Irvington — Begins May 8
Westchester Comedy Club Night (Young Adults / Nightlife) — Rye — May 14
Putnam County Events
- Rotary Rock & Roll Spectacular (Seniors / Young Adults / Live Music) — Mahopac — May 8
Dutchess County Events
Staatsburg Village Walking Tour (Senior‑friendly / Educational) — Staatsburg — May 8
Dutchess Handmade Spring Pop‑Up Shop (FREE / All ages) — Poughkeepsie — May 8–14
“Roséanity” Wine Weekend (Young Adults / Social) — Red Hook — May 8–10
Art Opening Reception (FREE / Arts / Seniors) — Poughkeepsie — May 8
Business & Home Expo (FREE / Community / Networking) — Dutchess County — May 9
SUNY Dutchess Concert (Young Adults / Community) — Poughkeepsie — May 9
Joe Jackson Concert (Young Adults / Music) — Bardavon Opera House — May 11
Leadership Dutchess Events (Professional / Young Adults) — Dutchess County — May 13
Rockland County Events
André–Arnold Affair Day Trip (Senior‑friendly / History) — Pearl River — May 9
“Remaking the Landscape” Exhibition (FREE / Arts / Seniors) — Nyack — May 9
NY Boulders 15th Anniversary Celebration + Fireworks (Family / Young Adults) — Pomona — May 9
6th Annual Plant Sale (FREE entry / Family / Seniors) — New City — May 9
Mother’s Day Farm Picnic & Activities (Family / All ages) — New City — May 10
Boulders School & Camp Day (Family / Kids) — Pomona — May 12
Frosty Tuesday Open Mic (Young Adults / Music) — Nyack — May 12
Bingo Night (Senior‑friendly / Community) — Pearl River — May 13
Orange County Events
Farm‑to‑Go Farmers Market (FREE / Family / Seniors) — Slate Hill — Starts May 8
Encaustics Art Exhibition (FREE / Arts / Seniors) — Wallkill — May 8–10
West Point Band Concert Series (FREE / Family / Seniors) — West Point — May 8 onward
Live Music at Pennings Farm (Young Adults / Social) — Warwick — May 8 onward
Spring into Downtown Newburgh Festival (FREE / Family / Young Adults) — Newburgh — May 9
Mother’s Day Cupcakes & Wine (Young Adults / Social) — Orange County — May 9–10
Spring Wellness Walk in the Park (FREE / Senior‑friendly) — Newburgh — May 12
“A Man Called Otto” Screening (Senior‑friendly / Community) — Orange County — May 8
Best Picks by Audience
Family Events
- Hudson River Spring Festival (Westchester)
- NY Boulders Celebration & Fireworks (Rockland)
- Spring Into Newburgh Festival (Orange)
Free Events
- Farmers Markets (region‑wide)
- Art Exhibitions (Westchester, Dutchess, Rockland)
- West Point Band Concerts (Orange)
- Yonkers Parade & Hudson River Festival
Senior‑Friendly
- Walking Tours (Dutchess)
- Historical Day Trip (Rockland)
- Bingo Nights & Wellness Walks
- Classical & community concerts
Young Adult / Social / Nightlife
- Wine events & cideries (Dutchess & Orange)
- Live music & open mic nights (Rockland)
- Comedy clubs & concerts (Westchester)
Hudson Valley–Wide Events for May
Major Festivals, Fairs & Signature Events
- Grand American BBQ Festival & Championship — Hudson Valley region — Early May (multi‑day)
- Rip Van Winkle Wine, Brew & Beverage Festival — Catskill — May 9
Seasonal & Recurring Spring Events
- Hudson Valley Farmers Markets (Season Opening) — Region‑wide — All month (weekly)
- Dogwood Acres Spring Fling (Spring festival series) — Hudson Valley — Weekends in May
- Indoor & Outdoor Spring Pop‑Up Shops / Markets — various towns — May (ongoing)
- Spring Flower Walks & Garden Events — farms, botanical sites — throughout May
Community, Fitness & Outdoor Events
- Kiwanis Kingston Classic (Community race) — Kingston — May (early month)
- Community Runs, Walks & Charity Events — multiple counties — throughout May
Arts, Music & Cultural Events
- Gallery Openings & Art Exhibits — Kingston, Hudson, New Paltz — May 2 onward
- Live Music Shows & Local Concerts — Hudson Valley venues — throughout May
- Theater & Performing Arts — region‑wide theaters — throughout May
Family‑Friendly Events
- Spring Farm Festivals & Agritourism Events — Hudson Valley farms — weekends in May
- Children’s magic shows, theater & performances — regional venues — throughout May
Food, Drink & Specialty Events
- Wine Tastings & Vineyard Events (Derby Weekend, Spring Events) — Hudson Valley wineries — early May
- BBQ Festival & Food Events — Hudson Valley region — May (select weekends)
- Local Food Truck Pop‑Ups & Artisan Markets — region‑wide — all month
Carnivals, Street Fairs & Local Festivals
- St. Patrick’s Carnival — Bedford (Westchester) — May 12–17
- Washingtonville KofC Carnival (Memorial Day Weekend) — Washingtonville — May 21–25
- Sloatsburg Carnival (Memorial Weekend) — Rockland County — May 21–24
Markets, Pop‑Ups & Shopping Events
- Weekly Farmers Markets — Peekskill, Beacon, Pleasantville, Kingston, etc. — every week starting May
- Artisan & Craft Markets — Hudson Valley towns — weekends throughout May
- Antique & Vintage Fairs (including Rhinebeck show) — region‑wide — May weekends
Hudson Valley–Wide Events for June
Festivals, Fairs & Big Community Events
- Rhinebeck Crafts Festival (Major artisan fair) — Rhinebeck (Dutchess) — June (annual)
- Festival at the Falls (Family festival) — Wappingers Falls (Dutchess) — June 7–8
- Beacon Strawberry Festival (Free / Family) — Beacon (Dutchess) — June 8
- Dutchess Community Carnival (Free entry) — Poughkeepsie — June 19–22
Cultural Celebrations & Parades
- Westchester Pride Festival — White Plains — June 7
- Juneteenth Celebrations (Music, food, culture) — Poughkeepsie & Hudson Valley locations — June 18–19
- African‑American Cultural Heritage Celebration — Valhalla (Westchester) — June 28
Music, Arts & Performing Arts
- Westchester Magazine Wine & Food Festival — Westchester County — June 9–14
- RiverArts Music Tour — Westchester — June 6–7
- Hudson River Music Festival — Westchester — June 21
- Free Summer Concert Series (“Alive at Five” & regional concerts) — across Hudson Valley — June (weekly)
Theater, Tours & Family Activities
- “The Wizard of Oz” Live Production — Rhinebeck — June 6–29
- Open Studio Tours (Arts / Free) — Peekskill — June 6
- Garden Tours & Historic Site Events — Untermyer Gardens, Sunnyside, Hudson Valley estates — throughout June
Outdoor & Recurring Events
- Bicycle Sundays (Free) — Bronx River Parkway (Westchester) — June Sundays
- Hudson Valley Food Truck Festivals & Markets — multiple locations — throughout June
- Farmers Markets & Outdoor Pop‑Ups — region‑wide — all month
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