Halloween Family Pumpkinfest


Westport, CT

The WDMA is excited to partner with the Westport Parks and Recreation Department to bring a safe and socially distanced family pumpkin activity to Main Street for the first 100 families who register.

The lower block of Main Street (from Post Road to the Vineyard Vines building) will be closed to traffic and parking to ensure plenty of room for the pumpkin tables to be appropriately spaced.

Please wear a costume and join in the Halloween spirit! (Just like the parade would have requested, please leave costume weapons at home – thank you)

Register your family for a table in one of our four available time slots!
  • 12:00pm-1:00pm
  • 1:30pm-2:30pm
  • 3:00pm-4:00pm
  • 4:30pm-5:30pm

Family check in will be at the Post Road end of Main Street.

Tables include pumpkins and a brand new set of decorating items. You will take home your decorated pumpkins, any extra decorating supplies from your table, up to 3 selfies and a bag of orchard apples generously provided by Camp Playland of New Canaan.

Selfie stations will be located around the activity area with hand-painted, Halloween themed selfie scenes. MoCA Westport, One River and the Staples High School Art Department will each create one of these unique photo opportunities.

Recognizing this isn’t a “normal” Halloween, many community sponsors and merchants are supporting this event to bringing a little happiness to our kids in a difficult year! Please thank and support our sponsors back by patronizing their businesses!

If you would like to give back to the community, please bring boxes of Mac ‘N Cheese to help the 501 (c)3 organization “Filling In The Blanks,” a child nutrition program. You can also make a monetary donation at our check-in desk when you arrive.


The DMA will take photos (with permission) of family pumpkins and costumes for kid and adult winners to take home prizes of downtown bucks!

October 25

12:00pm - 5:30pm
Age: All Ages