At 3:30 p.m. on Friday, October 30, Garden Cinema will start a free showing of "It's the Great Pumpkin, Charlie Brown." By the time Linus gives up on the pumpkin patch, the free reflective treat bags will be going out on the City Common, and costumed kids will be making their way through downtown from shop to shop. Halloween falls on a Saturday this year, and Greenfield Recreation scheduled the downtown celebration a day early.
So Greenfield's big Halloween night is Friday. Downtown trick-or-treat, the Rag Shag Parade, a free family night at the Y and October's Arts Walk all happen in the same few hours, within a few blocks of one another downtown. Saturday the 31st is a different kind of day. It's the last Saturday of the outdoor farmers market and the fifth anniversary of a brewery on Wells Street. If you plan for both days, you can go to all of it.
Friday afternoon, hour by hour
The Recreation Department's schedule runs from 4 to 7:30 p.m. downtown. Several other organizations scheduled their Halloween events in the hours just before that, so the afternoon starts early.
- 2:30 to 4:30 p.m. The Teen Room Halloween Hang Out runs at Greenfield Public Library, 412 Main St. It's free for ages 13 to 20. At the other end of Main, Ford & Toyota of Greenfield holds a trunk-or-treat at 1 Main St. during the same two hours.
- 3:30 p.m. The free Charlie Brown screening starts at Garden Cinema.
- 4:00 to 5:30 p.m. Trick-or-treat at participating downtown businesses. Treat bags are free on the City Common.
- 4:00 to 7:45 p.m. The YMCA at 451 Main St. holds its Community Family Night, free and open to everyone. It includes gymnastics, the gym, gaga ball, a bounce house, the game room and family swim.
- 5:30 p.m. The Rag Shag Parade starts at the Mohawk Mall and ends at Energy Park, where the costume contest follows.
The contest has eight prize categories: Best Homemade, Funniest, Best Cartoon Character, Scariest, Cutest, Adult Open, Group/Family and Best Howl-O-Ween Costume. With Adult Open and Group/Family on that list, it's more than a contest for small children. A household that dresses up together has a category of its own.
The Y's own schedule keeps the evening going after the parade. Its Spooktacular Halloween program is for kids up to 12 with a parent or guardian. The Haunted Game Room is open from 4 to 7:45, the Ghostly Gym Boo-Bounce starts at 6, Pumpkin Patch Splash runs from 6:20 to 7:20, and Spooky Gymnastics Play runs from 6:45 to 7:45. If a family finishes the costume contest at Energy Park and still has energy left, the pool and gym are open for almost two more hours.
When the parade ends, the Arts Walk is just starting
The Greenfield Arts Walk happens on the last Friday of every month from April through November, and the last Friday in October is the 30th. So the city's Halloween celebration and the monthly arts night share the same evening downtown.
The arts events run during and after the parade.
- The Arts Walk vendor market, with local arts and crafts and live music, runs from 4 to 8 p.m. at Fiske Avenue Pocket Park, at Fiske Ave and Miles St. During the season, the vendor market is usually on Court Square. For this date, it's listed at the pocket park.
- LAVA's cafe and gallery at 324 Main St. is open from 5 to 8 p.m. Madhouse Multi-Arts names LAVA, Looky Here and Madhouse itself among the arts organizations that take part in the Arts Walk.
- Festa Dei Mori, listed as a "Day of the Dead Celebration for our Ancestors," runs from 6 to 8 p.m. at the Webb Building, 76 Hope St.
This makes a family evening easy to plan. Trick-or-treat downtown at 4, watch the parade at 5:30, go to the contest at Energy Park, then walk back toward Main and Fiske for the Arts Walk before it ends at 8. Adults who skip the parade can still use the parade's foot traffic, since downtown will be busy all evening.
For dinner after the parade, Four Phantoms Brewing at 301 Wells St. has a Patch Burger pop-up from 5 to 8 p.m. After that, the Fox Hill Board Game Club runs Friday Night Dice from 6:30 to 9. The brewery calls the game night "Greenfield's newest, favorite biweekly event." Bear's Den Bar at 5 Bank Row is also downtown. It opened in August in the former Seymour Bar space, as the Greenfield Recorder reported, so this will be its first Halloween season on Bank Row.
Saturday is the last day of the outdoor market season
Halloween itself starts in Court Square. The Greenfield Farmers Market runs every Saturday from 9 a.m. to 1:30 p.m., and its 2026 season runs from April 25 through October 31. That makes Saturday the final outdoor market of the year. If you've been meaning to stock up on a favorite vendor's goods before winter, Saturday morning is your last chance outdoors.
Greenfield Public Library is running a free pop-up at the market that morning, from 9 to 1:30. It offers library card services, quick tech help and a spooky-button activity. Garden Cinema is showing "It's the Great Pumpkin, Charlie Brown" again at 11 a.m. That gives anyone who missed Friday's free screening a second chance, and it fits between market stops.
In the evening, the focus moves to Wells Street. Four Phantoms turns five, and it's celebrating with a raw bar from Scott Shucks from 5 to 8 p.m. The oysters come from Padanaram Oyster Farm in Dartmouth, and the brewery says it will have five ciders and three lagers on tap. In its event listing, the brewery describes the night this way:
"We'd love for you to celebrate this milestone with us before your late-night Halloween parties. Or drop in for some early evening fun if your ideal holiday means being tucked into bed by 9PM."
According to Four Phantoms' events page, Scott Shucks often sells out, and preordering is encouraged. At 8 p.m., Lockjaw's Jazz Freak-out starts and runs until 9:30. It's the first local show by saxophonist Jonathan Lorentz since he moved to Greenfield. The show is all ages, with a suggested $10 donation.
Greenfield's Halloween events come in a clear order this year. The city's celebration falls on Friday, so Saturday is open for the season's final events: the market's closing morning, a matinee, an anniversary dinner and a jazz set that ends by 9:30.
The city hasn't posted separate neighborhood trick-or-treat hours for October 31 on its Halloween page. The schedule there covers only Friday's downtown events. If your street has its own Saturday-night routine, that's a matter for you and your neighbors.
Sunday, and the weeks after
Visit Greenfield's calendar lists no events for Sunday, November 1. That makes it a good day for a walk, but if you're heading to Poet's Seat Tower, adjust your plans. The city closed the tower because of structural deficiencies and hasn't set a reopening date. The area around it is still open.
After that weekend, the market's next season is still taking shape. The Greenfield Farmers Market site mentions a Winter 2026–2027 vendor application but doesn't list public dates or a location yet. Last winter's market met at Greenfield Public Library. It met on November 8 and 22 and December 6 and 20, then on the first Saturday of each month from January through April. That's only last year's pattern, and this winter's schedule may be different.
The Arts Walk has one more date. Since it runs through November on the last Friday of the month, the season's final walk should fall on November 27, the day after Thanksgiving, if the schedule holds. The October 30 walk is the next-to-last one, and it shares downtown with the parade.
At Ashton Realty Group, we keep track of Greenfield's calendar because it shows us the town we live and work in, from the Rag Shag Parade on Main Street to the last outdoor market in Court Square. If this weekend has you wondering what your own Greenfield home is worth, we're glad to look at it with you. Get a Free Home Valuation whenever it suits you, even after the costumes are put away.
