Westchester Moms’ Guide to Summer Fairs and Festivals


Summertime is just around the corner, and at the peak of Spring comes an explosion of outdoor fairs and festivals. We put together a list of some of our favorites in Westchester County and the Hudson Valley area. And as if the fun wasn’t reason enough for checking these out; many of these local family favorites are also huge fundraisers for the communities we love.

fairs and festivals

May 28th

Hudson Valley Shakespeare Festival Kicks Off
HVSF Theater Tent at Boscobel House and Gardens, 1601 Route NY-9D, Garrison, NY 10524
Monday, May 28, 10:30 a.m. to 12:30 p.m.
Free. RSVP Recommended.

June 1st – 3rd

Festa Italiana
Saint Anthony of Padua, West Harrison, NY 10604
Friday, June 1, 6 p.m. – 12 midnight
Saturday, June 2, 5 p.m. – 12 midnight
Sunday, June 3, 2 p.m. ‑ 10 p.m.
Rain or Shine.

June 2nd

21st Annual Asian American Heritage Festival
Kensico Dam Plaza, 1 Bronx River Parkway Road, Valhalla, NY 10595
Saturday, June 2, 12 p.m. – 6 p.m.
Free admission and parking.

Donahue Park, 99 Shore Road, Cornwall-on-Hudson, New York 12520.
Saturday, June 2, 11 a.m. to 6 p.m.
Free. Donations welcome.

June 2nd – 3rd

PLUS Polish Festival
89 Western Highway South, Tappan, NY 10983
Saturday, June 2, 11 a.m. – 10 p.m.
Sunday, June 3, 11 a.m. ‑ 10 p.m.
$5 per person, kids under 12 free. Free parking.

June 3rd

31st Annual Tarrytown Craft and Food Street Fair
Main Street, Tarrytown, NY 10591 
Sunday, June 3, 10 a.m. ‑ 5 p.m.
Rain or Shine.

32nd Annual Croton Summerfest
Old Post Road  & Grand Street, Croton-On-Hudson, NY 10520
Sunday, June 3, 1 p.m. ‑ 6 p.m.
The parade steps off at 12:45 p.m. and begins at Veteran’s Corners and ends in the upper Village.

5th Annual Nanuet Street Fair
Main Street, Tarrytown, NY 10591 
Sunday, June 3, 10 a.m. ‑ 5 p.m.

June 5th – 10th

8th Annual Wine & Food Festival
Visit website for details and various locations.
Tuesday, June 5 – Sunday, June 10th

June 7th – 10th

Fol-De-Rol Festival and Crafts in the Park
Wampus Brook Park, 41 Wampus Avenue Armonk, NY 10504
Evening Hours.
Details to come. See website for the latest.

June 9th

38th Annual Ossining Village Fair
Historic Downtown Ossining, 165 Main Street, Ossining, NY 10562
Saturday, June 9, 10 a.m. to 5 p.m.

June 16th – 17th

Clearwater: A Music & Environmental Festival
Croton Point Park, 1 Croton Point Avenue, Croton-On-Hudson, NY 10520
Saturday and Sunday, June 16 and 17
Gates open at 9 a.m.
Kids 11 & under get in for free.

June 19th – 24th

St. Ann’s Festival
25 Eastern Avenue, Ossining, NY 10562
Evening Hours.
Details to come. See website for the latest.

June 23rd

Rye Recreation Food Truck Festival
Rye Recreation Park, 281 Midland Avenue, Rye, NY 10580
Saturday, June 23, 1 p.m. – 5 p.m.

July 11th – 15th

Feast of Our Lady of Mount Carmel
155 Highland Avenue. Verplanck, NY 10596​
Wednesday, July 11 –  Sunday, July 15 6 p.m. to 11 p.m.

July 12th – 21st

178th Annual Orange County Fair
Wednesday, July 12 – Saturday July 21
More details to come. See website for the latest.

July 17th – 22rd

St. Augustine Italian Festival
381 N Highland Avenue, Ossining, NY 10562
Evening hours.
Details to come. See website for the latest.

July 27th, 28th, and 29th

47th Annual Putnam County Fair
Putnam Veterans Memorial Park, 201 Gipsy Trail Road, Carmel, NY, 10512
Friday, July 27, 12 p.m. to 6 p.m.
Saturday, July 28, 10 a.m. to 7 p.m.
Sunday, July 29, 10 a.m. to 5 p.m.
Rain or Shine. Free Admission. Free Parking.

August 4th – September 30th (Saturdays, Sundays, and Labor Day)

New York Renaissance Fair
600 Route 17A, Tuxedo Park, NY 10987
Saturdays, Sundays, and Labor Day, 10 a.m. – 7 p.m.
Rain or Shine.

August 21st – 26th

Dutchess County Fair
The Dutchess Fairgrounds, 6636 Route 9, Rhinebeck NY 12572
August 21-26, 10 a.m. to 10 p.m.

Is your family a summer fair and festival go-er? Let us know which ones you love in the comments!

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Leah lived in New York City for most of her life and moved to Westchester County in 2011 to blend and extend her family with an adorable high school Math teacher she met on Match.com. After 7 years of staying home and working part-time, she is back to the full time grind, commuting to the Bronx daily in her minivan a.k.a. trusty mommy wagon (this city girl’s first and only car). This full-time working, part-time blogging mother-of-4 seems to have it all together to the observer. In fact, part of this illusion is truly having the most amazingly resilient children a mother could ask for. Leah is an overthinking, jam pack the agenda, let loose when no one’s watching, be kind to your neighbor, sanity don’t fail me now kind of soul and she loves being a part of Westchester County Moms Blog. She strives to keep her kids super busy with a wide variety and good balance of academic, social, and athletic activities while desperately managing her home and budget.