From spooky parades to caramel apples and costume contests, Halloween season is in full swing across town. Everyone from toddlers to adults can find ways to celebrate over the next two weeks.
Trunk or Treat — Oct. 25 and 29
The Tri-M Music Honors Society will host its annual Trunk or Treat on Wednesday, Oct. 29, from 5–7 p.m. in the Wayland High School cafeteria (264 Old Connecticut Path). Kids can enjoy live music performed by students, spooky games, candy, and a chance to try out musical instruments. Costumes are encouraged, and a $5 per child donation (cash or Venmo) is recommended.
Families can also join the WCPA Trunk or Treat on Saturday, October 25, from 2 to 3 p.m. in the Wayland Community Pool parking lot, where participants decorate car trunks and hand out candy. Entry is free for members; visitors can make a small donation to participate.
Haunted House at Wayland HS — October 27
The Wayland High School Connect Program will transform the Field House into a haunted maze on Sunday, October 27, from 5 to 8 p.m. Students design and staff the experience each year, and it’s one of the town’s most popular pre-Halloween traditions. Donations support student programming.
Town Building Trick-or-Treat & Spook-tacular — October 27
The Wayland Recreation Department invites children ages 7 and under to the Town Building, 41 Cochituate Road, on Monday, October 27, from 3:30 to 4:30 p.m.
Town offices will be decorated for a “Halloween Spook-tacular,” and staff will hand out candy and small treats. Departments traditionally get into the spirit — from the “scary Treasurer” to the “spooky Assessor.” Admission is free.
Villa Caramel Apples — October 28 – November 2
For a tasty treat, The Villa Restaurant will offer homemade caramel apples all week from October 28 through November 2, available individually for $7 or by the half-dozen for $40.
Flavors include caramel, Reese’s, M&M, Snickers, Butterfinger, Oreo, chocolate chip, pistachio, and chocolate drizzle.
Dudley Chateau Halloween Costume Party — October 31
The Dudley Chateau will host its 16th annual Chat Halloween Costume Party on Thursday, October 31, from 8:30 p.m. to midnight at 20 Crest Road, Wayland.
Cash prizes of $100, $50, and $25 will be awarded for the top three costumes and everyone is encouraged to come dressed in their most creative attire. “See you there!” organizers said in their flyer, promising a lively night of music and fun.
Town Trick-or-Treating — October 31
Wayland does not set official town-wide trick-or-treat hours. Families are encouraged to follow the long-standing tradition of going door-to-door on October 31, regardless of weather. The town reminds drivers to be extra cautious throughout the day and evening.
