Table of Contents
Westchester County Events
Build the Thrill (LEGO Event) — LEGOLAND Discovery Center, Yonkers — May 1–May 7 (ongoing event)
Between the Lines Jr. (Theater) — Irvington — May 1–3
Mommy & Me: Animals & Nature — Westmoreland Sanctuary, Mount Kisco — May 1
Spring Crafts at Lyndhurst — Lyndhurst Estate, Tarrytown — May 2–3
Kala Samaagam Community Celebration — ArtsWestchester, White Plains — May 2
Genessa & The Selena Experience (Concert) — Paramount Theater, Peekskill — May 2
Pleasantville Farmers Market (Free entry / Family / Seniors) — Pleasantville — May 2
Rotary Duck Race Festival — Sprout Brook Park, Cortlandt Manor — May 3
Laurie Berkner Live (Family Concert) — Westchester County venue — May 3
Mom’s Night Out Event — The Westchester Mall, White Plains — May 7
Putnam County Events
No events
Dutchess County Events
Hudson Valley Fair (Family Festival) — Wappingers Falls — May 1–3
Dutchess Handmade Spring Pop‑Up Shop (Free entry / Family) — Poughkeepsie — May 1–7 (ongoing)
ACBL Sectional Bridge Tournament (Senior‑friendly / Community) — Poughkeepsie — May 1–3
Rhinebeck Antique Car Show & Swap Meet (Family / Senior‑friendly) — Rhinebeck — May 2–3
Poughkeepsie Farm Project Plant Sale (Free / Family) — Poughkeepsie — May 2
Miles of Hope Spring Brunch (Community / Senior‑friendly) — Dutchess — May 3
Rockland County Events
Uke‑a‑Palooza (Free / Family / Music) — The Angel, Nyack — May 2
Tea with Tiffany’s (Free / Senior‑friendly / Educational) — Haverstraw — May 2
Dancing in the Streets Outdoor Concert (Free / Family) — Nyack — May 2
Returning to Belonging (Poetry & Music / Arts) — Rockland Center for the Arts, West Nyack — May 2
Frosty Tuesday Open Mic (Community / Low cost) — Nyack — May 5
Orange County Events
Star Wars Trivia Night (Community / Family‑friendly) — Clemson Brewing Co., Middletown — May 1
Hudson Valley Mac & Cheese Festival (Family Food Festival) — Brotherhood Winery, Washingtonville — May 2
SUNY Orange Community Orchestra (Senior‑friendly / Arts) — Middletown — May 2
Newburgh Urban Farming Fair (Free / Family / Community) — Newburgh — ~May 2–3 timeframe
“Michael” Film Screening (Senior‑friendly / Accessible) — Paramount Theatre, Middletown — May 6
Words & Music Tour (All ages / Community) — Goodwill Church, Port Jervis — May 7
Quick Highlights
- Top family picks:
- Hudson Valley Fair (Dutchess)
- LEGO Build Event (Westchester)
- Mac & Cheese Festival (Orange)
- Best free events:
- Uke‑a‑Palooza (Rockland)
- Kala Samaagam (Westchester)
- Farmers Markets (Westchester & Dutchess)
- Best senior‑friendly:
- Antique Car Show (Dutchess)
- Tiffany Tour (Rockland)
- Orchestra concert (Orange)
Hudson Valley–Wide Events for May
Major Festivals, Fairs & Signature Events
- Hudson Valley Fair — Heritage Financial Park, Wappingers Falls — May 1–3
- Rhinebeck Antique Car Show & Swap Meet — Dutchess County Fairgrounds, Rhinebeck — May 2–3
- Hudson Children’s Book Festival (Free / Family) — Hudson — May 2
- Spring Crafts at Lyndhurst (Large craft festival) — Tarrytown — May 1–3
- Grand American BBQ Festival & Championship — Hudson Valley region — Early May (multi‑day)
- Apple Blossom Festival — Fishkill Farms, Hopewell Junction — May 3
- 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
- Hudson Valley Marathon, Half & 10K — Walkway Over the Hudson — May 3
- Kiwanis Kingston Classic (Community race) — Kingston — May (early month)
- Community Runs, Walks & Charity Events — multiple counties — throughout May
Arts, Music & Cultural Events
- Catskill First Friday (Art / Music / Free community event) — Catskill — May 1
- Athens Cultural Center First Friday Exhibition — Athens — May 1
- 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
- Hudson Children’s Book Festival (Free) — Hudson — May 2
- Apple Blossom Festival (Farm + family activities) — Hopewell Junction — May 3
- 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
- Hudson Valley Mac & Cheese Festival — Brotherhood Winery, Washingtonville — May 2
- 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
- Chester PBA Carnival — Chester (Orange County) — Apr 29–May 2
- 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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