Family

A parent panel will share helpful resources, lessons learned, and self care strategies for navigating a loved one's substance use disorder and addiction.

A free 3-part series offering connection, education, and hope for parents, caregivers and loved ones.

A free 3-part series offering connection, education, and hope for parents, caregivers and loved ones.

A free 3-part series offering connection, education, and hope for parents, caregivers and loved ones.

Hop on over for some family fun! Meet the Easter Bunny, win prizes & help the EnKA Food Pantry stock their shelves! Please bring a box of cereal to donate.

Schedule:

• Friday: Fairgrounds open: 4pm to 10 pm
• Saturday: PARADE 9:15 am
• Fairgrounds open: 10 am to 9 pm

Online tickets sales now open – click here to buy sheets of tickets online!

In-person tickets sales – whole sheets only –  will be available at a booth on the Fairgrounds in the Winchester Town Hall parking lot. Cash or credit card.

• Thursday, May 15  — from 12 noon until 6 PM  
• Friday, May 16 —  from 8:30 AM until 4:30 PM. 

In May, 1935 the En Ka Society held its first street fair. It was a novelty to Winchester and was a huge success, attracting thousands. It has grown from a single ride and a

Second day of a two-day event!

In May, 1935 the En Ka Society held its first street fair. It was a novelty to Winchester and was a huge success, attracting thousands. It has grown from a single ride and a few games into a much anticipated occasion. Generations of families in Winchester and surrounding communities have attended and continue to support tradition.

Continuing to this day, the En Ka Fair marks the beginning of summer for many citizens, old and young alike. We hope you will join us in May for this fun-filled event! 

Join us on the lawn for lawn games (and maybe some cool treats) to wrap up our 2026 Summer Reading Program. For kids in PreK (age 4) -rising 6th grade. Registration required. Questions? Email winchild@minlib. net, call (781) 721-7171 x326, or visit the Children's Room for more information.

Please join FAN for our first event of the 2026-2027 year, Families & Fire Trucks! This fun, family-friendly event is scheduled for Saturday, October 3, 2026, from 10:00-11:30 AM (rain date: October 10) and is free for FAN Members and all families in the community. Children will be able to see different trucks and vehicles from Winchester Fire Department, Police Department, Department of Public Works, Mobile Whinnies, and a special guest car: Lightning McQueen! The Amushe Cafe truck will be selling coffee to enjoy as you walk around.

Please join FAN for our very first event of the 2025–2026 year, Families & Fire Trucks! This fun, family-friendly event is free for FAN Members and all families in the Winchester community.

The event is scheduled for Saturday, September 27, 2025, from 10:00–11:30 AM (rain date: October 4). Parking will be available in the lot behind the school and side streets as the main lot will be closed for the trucks.

Please register for the event using the event link or visit www.fanwinchester.org to learn more about FAN. If you have any questions, please contact childrensevents@fanwinchester.org.