Wessie Fest kicks off seasonal downtown events

Aerosol artist Mike Rich will be working to complete his "Greetings from Westbrook" mural during Wessie Fest this Saturday, Oct. 22. On Monday, he was about halfway done with the project at Greater Portland School of Jukado. 

Energy is growing in downtown Westbrook, and it’s just in time for autumn festivities – and yes, the start of the holiday season.

The first-ever “Wessie Fest,” celebrating the now-famous mythical snake, will take place this Saturday, Oct. 22, and will kick off a slew of upcoming events downtown.

Wessie Fest, organized by the Downtown Westbrook Coalition, will feature a full day of activities based in Blue Note Park, including a “Wessie Pie-Thon” pie baking contest, “Wessie Toss” corn hole, a sidewalk parade, photos with a live snake, crafts and vendors, including the International Cryptozoology Museum.

The majority of festival events will run from 10 a.m.-2 p.m., including food trucks and Mast Landing Brewing Co. opening at noon. At 2 p.m., TV personality Bill Brock, of “Monsters Underground,” will host a talk about Wessie and other mysterious creatures, followed by a “Wessie Hunt” at 3 p.m. Later that night, the Jason Spooner Band will play at Mast Landing Brewing Co., 920 Main St., at 7.

Meanwhile Saturday, Mike Rich, a well-known graffiti artist, is also set to be putting the final touches on his “Greetings from Westbrook” mural along the side of Greater Portland School of Jukado.

The mural, inspired by the iconic postcard imagery and a similar project in Portland, is already underway and can be seen from Main Street. Each block letter (five so far) has been filled with some of Westbrook’s most well-known landmarks and people. The mural has been sponsored by Westbrook Arts & Culture and area businesses, and is intended to bring public art to the downtown.

Andy Curran from Westbrook Arts & Culture said four bands are scheduled to appear Saturday in the gazebo near where Rich will be working, adding another festive feel to Wessie Fest and the mural project.

Westbrook country and bluegrass legend Al Hawkes will highlight the event, debuting a song about Wessie. Bluegrass band Cumberland Crossing, Pete Witham and Matt Brunner will also perform.

Next weekend, the Halloween holiday will take over the downtown, and will feature the return of Halloween on Main Street after a one-year hiatus. The popular trick-or-treating event, which closes a large portion of the street from 4:30-6 p.m., normally attracts a few thousand residents. Coinciding is Pumpkins in the Park, which will also use Blue Note Park in Westbrook Common for its lit jack-o-lantern walk.

That same day, the Downtown Westbrook Coalition will also kick off a holiday pop-up market in Blue Note Park from 3-7 p.m., which will run through the holiday season. The market will feature a number of local businesses selling products in one convenient location. It will be open Sundays from noon-5 p.m., Tuesdays and Wednesdays from 4-7 p.m., and Thursdays from 11 a.m.- 7 p.m. through the week of Dec. 11.

Abigail Cioffi, the coordinator of the Downtown Westbrook Coalition, said the group is hoping to have featured vendors on Thursdays, such as local authors or civic organizations.

So far, she said, Greetings from ME, Martha Grubb Crafts, and representatives from Mary Kay, LuLaRoe, Paparazzi, Posh, and Usborne Books have registered for the market.


“Wessie Fest” – Saturday, Oct. 22 in Blue Note Park. The festival and vendors will be operating from 10 a.m.-2 p.m. Bill Brock of “Monsters Underground” will host a talk and Wessie hunt starting at 2 p.m.

Halloween on Main Street will return on Friday, Oct. 28 from 4:30-6 p.m. The second annual Pumpkins in the Park event, with a “haunted pumpkin walk” will take place simultaneously Friday in Blue Note Park, and will remain open until 7 p.m.

The holiday pop-up market launches Oct. 28 from 3-7 p.m. in Blue Note Park. Anyone interested in being a vendor can contact Cioffi at abigail@downtownwestbrook.com or 391-2977.


Aerosol artist Mike Rich will be working to complete his “Greetings from Westbrook” mural during Wessie Fest this Saturday, Oct. 22. On Monday, he was about halfway done with the project at Greater Portland School of Jukado.