All Set for Memorial Day Weekend

Weston Today photos

May 15, 2026  |  by Ted Craft

Weston’s traditional Memorial Day Weekend kicks off on Friday, May 22 with the opening of the popular fair, followed by the 5K Road Race on Saturday, music at Route 57 WestFest on Saturday and Sunday, and the fire department’s annual parade on Monday.

The Fair, Friday May 22 – Monday May 25

The always popular fair, held on the Hurlbutt Elementary School grounds, features hot dogs, cotton candy, games, and of course, rides. Bracelets for unlimited rides are available on presale here.

Fair hours are:

Sensory-friendly editions of the fair run on Saturday and Sunday from 1:00 to 2:00 both days.

Route 57 WestFest

Saturday and Sunday’s editions of the fair are accompanied by accompaniment, the Route 57 WestFest music festival, wall-to-wall performances by 18 acts on a top-notch stage with professional sound engineering.

Closing out the show on Saturday evening (at 8:30) is the Good Godfrey band, and at the same time on Sunday evening the Eliot Thompson Band wraps up WestFest.

The 5K, Saturday May 23

At 8:30 am, hundreds of runners, joggers, and walkers take to the streets in the 5K Road Run/Walk each year. The USATF certified scenic course goes around the center of town.

At 7:45, a Kids Fun Run starts on the high school track: a 100-yard dash, a quarter-mile race, and a one-mile race.

New this year for the 5K: a three-wave timed start to create a smooth experience for runners and walkers of all speeds. Your official race time will begin when you cross the start line and end when you cross the finish.

You can sign up for the 5K and Fun Run online here.

And, if you also register by May 31 for October’s Kiwanis Reservoir Run, you will have a chance to win two free round trip Jet Blue tickets to wherever the airline flies. Sign up for that here.

The Parade, Monday May 25

The Memorial Day Parade is put on by the Weston Volunteer Fire Department. It begins in front of Weston High School at 10:45, proceeds down School Road to Weston Road (Route 57), then goes up to Norfield Road, turns left, and ends at the Town Hall campus.

It’s a good idea to get there early, before traffic is controlled on the route and the best parking spaces are already taken.

After the parade, a memorial ceremony is held on the Town Green in front of Town Hall. Then, Fire Department volunteers give out free hot dogs at the firehouse, and the Memorial Day Fair begins its final session.