The Wayland Festival will fill the Town Center green with music, art, food, and family activities on Saturday, October 4. Running from 11 a.m.–6 p.m. at 35 Andrew Ave., the free event has grown from a student-led idea into one of the town’s largest cultural gatherings.
The festival traces its origins to 2019, when Wayland students Joss O’Heron, Ellie Barenboym and Kyra Spooner gained Town Meeting approval to produce a community arts event. The pandemic delayed their plans until 2022, when the first Arts Wayland Expo finally took place. Since then, attendance has steadily grown, with more than 3,000 people turning out in 2023.
Producer Chris Reynolds, a longtime resident and entrepreneur, has been central to the festival’s expansion. Reynolds is co-founder and CEO of Vascular SafeGuard, a medical device company that collaborates with pediatric hospitals. His career spans roles in energy technology, information security and startup leadership. That experience in building ventures from scratch has informed how he manages the complexity of organizing a large-scale public festival.
This year’s festival is expected to be the largest yet. Organizers have confirmed:
- 30 food trucks and tables serving a wide range of cuisines
- 60 vendor tables offering crafts, goods, and local services
- 30 artist booths featuring painters, sculptors and artisans from Wayland and surrounding towns
- A golf cart “train” ride to move families and children around the festival grounds
- A parade with historical reenactors, including costumed musketeers, to commemorate the nation’s 250th anniversary
The entertainment schedule includes headliner Dwayne Haggins, whose music fuses Americana, R&B, and country. He will be joined by Chris Nyfong, Sway Island, Delila, and the Wayland High School Honors Jazz Ensemble under director Joe Oneschuk. Two dance troupes are also slated to perform.
A community collaboration
The festival is supported by a broad coalition of groups, including Arts Wayland, the Town of Wayland, Village Bank, Wayland METCO, the Human Rights, the Diversity, Equity, and Inclusion Committee, the Wayland Museum and Historical Society, the Rev250 Working Group, the Greater Boston Chinese Cultural Association, the Wayland Post and a number of local foundations and businesses.
This year’s festival imagery features “W of United Hands,” created by Wayland High School graduate Alyssa Ao, symbolizing community collaboration.
For Reynolds, the significance of the event is measured not just in attendance but in how it brings the town together. “This is about giving the community a reason to gather, to share culture and history, and to create new memories,” he has said.
The Wayland Festival 2025 opens on October 4 and is expected to draw thousands of visitors, marking another milestone in a community tradition that began with the initiative of three middle school students more than six years ago.
