Easton Preparing to Greet the Season with Fall Kickoff

Carve out some time to be in Downtown Easton for their annual Easton’s Fall Kickoff on October 2nd and 3rd.
Occurring each year on the first Friday and Saturday of October, Fall Kickoff invites locals and tourists alike to shop, dine, and stroll the giant pumpkin trail in downtown Easton, taking in a bevy of family-focused activities to help ring in the colder seasons. This free event offers pumpkin painting, fire juggling, live music, an outdoor movie night, and more, all free and open to the public.
The cornerstone of Fall Kickoff is the giant pumpkin trail; a winding path of over 60 pumpkins, each over 50lbs and professionally carved and set out on display for guests to peruse as they enjoy the charm of downtown Easton in the Fall. “It really changes the tone of the whole town for the rest of the year,” said Tom Maglio, Marketing and Events Manager for Easton Economic Development Corporation. “It’s impossible to look at a street filled with these giant pumpkins and not feel excited about fall.” Highlights from last year include a beautiful mermaid, a pirate, and a whole yard of smiling giant pumpkins in braces. Maglio felt confident that this years would improve even further upon last years. “You always want to top what you did before. Our big set piece in 2025 was a giant crab made of pumpkins, and we’re determined to outdo ourselves as far as displays go for 2026.”
Maglio also underlined the importance of events like this to local merchants in town. There is a concentrated effort downtown for shops and galleries to offer sales, specials, and their own independent events, encouraging shoppers to see what’s new and exciting for the fall season. With the event further enhanced by live outdoor music in the evening Friday and during the day Saturday. Many downtown restaurants will offer autumn-inspired specials and cocktails. “We all come together to show our neighbors what makes living in and near this town so great. It’s such a joyous time to be here.”
October’s First Friday Gallery Walk is also a great opportunity to discover incredible, vibrant pieces from many talented artists, making Friday evening a perfect start to the festivities.
Easton’s Fall Kickoff remains an event focused on setting Easton as a backdrop to family fun. There has been a renewed focus on two particular areas of town: The Academy Art Museum at 106 South Street and the Talbot County Free Library at 106 W Dover Street.
The Academy Art Museum will host free pumpkin decorating and, new this year, glass pumpkin demonstrations by the Glass Half Full mobile glass studio. Further attractions include live music, libations and food from local businesses, and a free movie night with an outdoor screening of Hotel Transylvania on Friday evening.
Easton Talbot County Free Library to host a kids and family activity center that Saturday between 10 am and 2 pm, where local businesses and non-profit with gather to offer free activities and giveaways. “Both spots have become very popular last year, and we want to keep adding more and more to them. It gives parents a chance to relax and let the kids have as much fun as possible between going through the pumpkin trail,” Maglio said.
Easton Economic Development Corporation was launched in 2013 to drive economic vitality, smart redevelopment, and business creation in the historic Town of Easton, Maryland, to foster a healthy quality of life for all generations. The Easton EDC works to catalyze Greater Easton’s continued prosperity as a diverse and healthy “smart town,” leading innovation where the land and water meet.