Weekend at a Glance: Walking Tour, Last Farmer’s Market, Halloween parades & parties, Outdoor Movie, and Fall Fun on the Farm

by beth on October 22, 2021

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Above: If you’re heading to the SFA Halloween parade and party (with costume contest), you may want to bring a candy bucket, since Rec’s “Trunk or Treat” immediately follows. (photos by Susan Fitzgerald and Beth Melo)

There is a lot going on in Southborough this weekend. Most, but not all of it, is Halloween-themed fun. Here’s a reminder of the highlights:

Saturday, October 23, 2021

  • Fay School Farmer’s Market (9:00 am – 12:00 pm) @ Fay School, parking at Brackett House, 31 Main St: The school is featuring a farmer’s market with vendors selling a variety of foods and goods. Plus (as detailed below), the market is hosting the Library’s Halloween Party. For details, see dedicated post.
    • Southborough Library’s Halloween Party for Kids (9:00 am – 12:00 pm) @ Fay School Farmer’s Market: Fay School will host the Southborough Library’s annual Halloween party at their Farmer’s Market. This is free and open to all ages, no registration required. The event will include Halloween games and crafts, plus a Halloween story time, costume parade, and children’s concert. For schedule and details, see dedicated post.
  • Historic Walking Tour: Model Farms and Country Seats (1:00 – 3:00 pm) @ Main Street: Southborough Historical Society is hosting two tours of the Historic Main Street area this month. This one will focus on the development of West Main Street as an area of vast summer estates for Boston’s wealthy elite. Advanced registration is required and limited. The tour is free to SHS members or $15 for non-members. For details, see dedicated post.
  • Town hosted Halloween Fun (3:30 – 7:40 pm) @ at Woodward Campus and the Public Safety Complex
    • SFA Halloween Parade (3:30 – 4:30 pm) @ Woodward School to the Public Safety Building: Southborough Firefighters Association is hosting their free annual Halloween Parade and party with costume contest. Marchers are asked to line up at Woodward School. From there they’ll march to the Public Safety Building. No registration required. For details, see dedicated post.
    • Trunk or Treat (4:30 – 6:00 pm) @ Woodward School parking lot: Southborough Recreation is inviting kids to trick or treat at an array of cars lined up with trunks open, decorated in Halloween spirit. Free, no registration required. For details, see dedicated post.
    • Outdoor Movie Night – Monster’s Inc (6:00 – 7:40 pm) @ Choate Field – in front of Woodward School: Southborough Recreation is putting on a free outdoor movie night, screening Monster’s Inc. The movie is rated G. No registration required. For details, see dedicated post.

Sunday, October 24, 2021

  • Fall Fun on the Farm (12:00 – 4:30 pm in 90 minute windows) @ Chestnut Hill Farm: Enjoy a classic New England fall day featuring apple cider, hayrides, a climbing haystack, live music, scenic walking trails, a Storywalk, and a visit to see the goats, chickens and sheep. Indulge in yummy food, apple cider, and other seasonal treats available for purchase. Pre-registration (and fee) required. For details, see dedicated post.

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