Main Street Old Saybrook

Hop down Main Street for the Kids Bunny Hop! Grab a basket, visit local shops for treats, and meet the Easter Bunny along the way, limited baskets available, so don’t wait!

After careful consideration, the Chamber has made the tough decision to cancel — and hopefully reschedule — the 29th Annual Old Saybrook Chili Fest that was to be held on Saturday, February 28, 2026.

Celebrate fall at Old Saybrook’s Great Main Street Pumpkin Festival with crafts, activities, music, shopping, tasty treats, a scavenger hunt and festive fun for the whole family. Costumes encouraged.

Old Saybrook Main Street Ladies Swag Stroll September 25th 5–8 Purchase a $10 tote bag Grab your girlfriends and stop into more than 10 participating businesses to pick up your “swag” gifts plus earn tickets to enter to win a gift basket filled with goodies! Bags available at Cottage Flair Only 100 will be sold! […]

Kick off summer at the 3rd annual Celebrate Saybrook Street Party. Main Street will be closed and filled with live music featuring Sugar, Jamie's Junk Show and Jeremy Haddad. Enjoy delicious food, CT-made craft beer and spirits, and an exciting mix of vendors and lots of family fun.