Photo Courtesy discovereaston.com
Easton, MD - Shop, dine, and stroll the giant pumpkin trail in downtown Easton during Easton’s Fall Kickoff on October 2nd and 3rd, 2026!
Talented artists from IceLab will once again fill the streets with pumpkin art, and shops and galleries will be open and ready to help you get into the fall spirit. Friday night and Saturday will feature live outdoor music, and many downtown restaurants will offer autumn-inspired specials and cocktails.
October’s First Friday Gallery Walk will be a great opportunity to discover vibrant pieces from many talented artists. For All Seasons will host an autumn porch party with refreshments and fall fun at 111 East Dover Street Friday evening. Families can also catch Cascading Carlos juggling fire in Thompson Park Friday night from 5 pm to 7 pm and Saturday from 12 pm to 4 pm.
The fifth annual Easton Fall Craft Fair will be held at Trinity Cathedral on October 3rd from 10 am to 3 pm. Visitors can enjoy a variety of handmade items, including jewelry, pottery, art, woodwork, and apparel from over 30 local artisans. On the same day, the Hot Rods and Hose Car Show will take place from 9 am to 2 pm at 315 Leonard Rieck Drive. This event features classic cars, hot rods, custom trucks, and fire trucks displayed at the Easton Volunteer Fire Department, offering entertainment for car enthusiasts and a selection of food for purchase. All proceeds benefit the EVFD.
Easton EDC will also partner with the Talbot County Free Library to host a kids and family activity center during the festivities on October 3rd between 10 am and 2 pm, featuring giveaways and activities from For All Seasons, Two Pair Collectibles, Talbot Humane, and more.
Families and friends can come down to the Academy Art Museum for a free movie night with an outdoor screening of Hotel Transylvania on Friday at 8 pm and free pumpkin decorating from 4 pm to 7 pm Friday and 10 am to 2 pm on Saturday. The Academy will also host glassblowing demonstrations from the Glass Half Full Mobile Glassblowing Studio on Saturday from 10 am to 2 pm.
“The Academy Art Museum is delighted to partner with Discover Easton to help bring our town to life for Fall Kickoff,” said Charlotte Potter Kasic, Executive Director of the Academy Art Museum. “Easton really shines during this event because of how much everyone embraces the season and works together to make downtown a special place for the people that live here and visit here. It’s wonderful to see the community come together to celebrate and make this time of year so memorable for everyone.”
There are so many ways to kick off fall in downtown Easton! For more info on this activity-packed weekend and a map of the event, click the link: https://discovereaston.com/fallkickoff/
