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Summer 2023 Guide to Festivals and Fairs in Westchester and Beyond

UPDATED There is so much fun to be had this summer!

By Kelly Fitzpatrick August 29, 2023

Summer 2023 is shaping up to be a great one for family fun!  There are so many festivals and fairs in Westchester County and beyond.  Many of these Westchester County fairs and festivals are annual events and draw a large crowd.  Some of them are specific to parts of the season, such as the beloved Chappaqua Strawberry Festival.  If you are looking to stay close to home or don't mind driving to an attractions like festivals or fairs, we've got quite a line-up of events to choose from to make summer 2023 one for the books!  We wish you a summer filled with family fun and great memories.

This article will be updated often, so be sure to check back frequently as new dates are announced!

Updated August 28th


August Festivals and Fairs



HVSF – The Hudson Valley Shakespeare Festival. (hvshakespeare.org)

Garrison

Henry V - through August 21st

Love's Labor Lost - through August 27th

Penelope - September 2nd - September 17th


St. Leo's Fair

Stamford

August 29th - September 2nd


Renaissance Faire

Tuxedo Park

August 26th - October 8th



September Festivals and Fairs



5th Annual Sunflower Festival at Barton Orchards

Poughquag

September 1st – 4th


32nd Annual Balloon Festival

Lagrangeville

September 1st - 3rd


Hudson River Festival

Croton

September 2nd


Greenburgh Block Party Back to School Backpack Giveaway

White Plains

September 2nd


Pound Ridge Artisan and Vintage Flea

Pound Ridge

September 4th


HVSF – The Hudson Valley Shakespeare Festival

Garrison

Penelope - September 2nd - September 17th


Renaissance Faire

Tuxedo Park

August 26th - October 8th


Mount Kisco Septemberfest

Mount Kisco

September 8th, 9th, 10th


City of White Plains Truck Day

White Plains

September 9th


Lewisboro Library Fair

North Salem

September 9th


Bedford Fire Department Parade, Party and Fireworks

Bedford Village

September 9th


Oktoberfest at Barton Orchards

Poughquag

September 9th – 10th


Yorktown Grange Fair

Yorktown

September 8th - 10th


Bluegrass at the Farm

Harvest Moon Farm, North Salem

September 14th


Flip Circus at Danbury Fair Mall

Danbury

September 15th - 25th


Oktoberfest with Captain Lawrence Brewing Company at Cross County Shopping Center

Yonkers

September 16th


Mountain Creek Oktoberfest

Vernon, NJ

September 16th & 17th


Giant Tag Sale

Mount Kisco

September 22nd and 23rd


Family Campout

Pound Ridge

September 23rd - 24th


Pleasantville Block Party

Washington Ave and Wheeler Ave

September 23rd, Raindate September 30th


Hudson Valley Apple Festival at Barton Orchards

September 23rd – 24th


Rye Children's Book Festival

September 23rd


Soul Brewing Company Oktoberfest

Pleasantville

September 23rd and 30th


Sound on the Sound

Bridgeport, Connecticut

September 30th - October 1st


Chappaqua Children's Book Festival

September 30th 10 a.m. - 4 p.m.


For even more summer fun check out our other Summer Fun Guide favorites:





Interested in growing this guide?  There's always room for more fairs and festivals!  Email mackidchappaqua@macaronikid.com

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