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Crabapple's Holiday Season Now Runs on Thursday Nights

Until this year, Milton's holiday season downtown had one fixed date: Christmas in Crabapple on a December Saturday, with Santa, music and the tree lighting at Broadwell Pavilion at dusk. That event is still on the calendar. Now it sits inside a five-week run of downtown dates, and four of the five fall on a weekday.

What changed is a food truck series that did not exist before mid-October. In an October 22 news post, the City of Milton calls Wanderlust Food Truck Fest "a new addition this fall to our community's culinary scene." Its remaining dates are planned so that Crabapple has something on a Thursday evening before, during and after the tree lighting.

Date Day Event Where Hours
November 12 Thursday Wanderlust Food Truck Fest Market District Crabapple parking area and Crabapple Market gravel lot 4 to 8 p.m.
November 13 Friday Holiday Market Shop, Sip & Stroll The Green at Crabapple Market 1 to 5 p.m.
December 3 Thursday Wanderlust Food Truck Fest Same two lots 4 to 8 p.m.
December 5 Saturday Christmas in Crabapple Broadwell Pavilion, 12615 Broadwell Road 2 to 6 p.m.
December 10 Thursday Wanderlust Food Truck Fest Same two lots 4 to 8 p.m.

How a weeknight food truck series got into the holiday calendar

Wanderlust started on October 15, from 4 to 8 p.m. It set up in two places in downtown Crabapple: the Market District Crabapple parking lot and the gravel area behind the Green at Crabapple Market. A second edition followed on October 29. Appen Media reported that the opening night had more than a dozen trucks. Admission is free, and you pay each truck directly.

The City has said the menu will be different each time. In that same post, which asks more vendors to sign up, Milton wrote that "each event will be a little different depending on the collection of that night's food trucks," and pointed truck owners to the Eventeny application page for the November and December dates. That same page lists the City of Milton as host.

With trucks on November 12, December 3 and December 10, Christmas in Crabapple lands two days after one Wanderlust night and five days before the last. The two lots used for the trucks are a short walk from Broadwell Pavilion, so all five dates happen in the same few downtown blocks.

November 12 and 13 run back to back

The first holiday date of the season is two days in a row. On Thursday, November 12, Wanderlust returns to both lots from 4 to 8 p.m. The next afternoon, Crabapple Market's calendar lists a Holiday Market Shop, Sip & Stroll on The Green from 1 to 5 p.m.

The Friday afternoon time slot makes sense given the shops around The Green. Crabapple Market's shopping directory lists these merchants:

  • Poe & Company Bookstore
  • Indigo Home & Design and Indigo Home & Apparel
  • The Twisted Thread
  • Ameline Shoppe
  • For Something Beautiful
  • Whitetail Bicycles
  • Woof Gang Bakery & Grooming
  • Creative Journey Studios
  • Metamorphosis Fine Arts & Crafts Gallery, which the directory lists as open at 1870 Heritage Walk

If you shop early for the holidays, that Thursday and Friday give you two separate trips downtown: dinner from the trucks one evening, then the shops on Heritage Walk the next afternoon.

December 5 is still the big day, with Thursdays on either side

Christmas in Crabapple runs from 2 to 6 p.m. on Saturday, December 5, along Broadwell Road. In its Kids Market announcement, the City calls it Milton's "traditional kickoff to the yuletide season." Santa poses for photos, and the afternoon ends with the lighting of the City's official Christmas tree at Broadwell Pavilion. The tree lighting is at dusk.

The new part this year is a Kids Market. Sellers ages 5 to 17 get a table to sell things they have designed, baked or crafted. The City runs it with the same group that runs the Kids Market at Crabapple Fest, and registration is through Kids Markets. In the same announcement, the City said Christmas in Crabapple "typically draws about 1,500 people." It also noted that the event's footprint along Broadwell Road is limited, which is why it encouraged families to sign up early.

About 1,500 people in four afternoon hours, on one stretch of Broadwell Road, is what Christmas in Crabapple has been for years. The Thursday nights that come with it this season are smaller and run four hours each. They let you see downtown dressed for the holidays without the Saturday crowd, either two days before the tree lighting on December 3 or five days after on December 10.

Places to sit down between the scheduled nights

The trucks take up the lots three evenings. On other nights, the downtown restaurants are the draw. On publish day, this is where things stand:

  • MilkShake Factory, 12660 Crabapple Road, Suite 110, marked the first anniversary of its Milton location on September 12, 2026, according to QSR Magazine.
  • Yum! Thai Cuisine & Bar, 3100 Heritage Walk, Suite 102, was on Milton's agenda for an alcohol license hearing in January 2026, per a City of Milton meeting preview. Its website lists it as open Tuesday through Sunday.
  • Market District Crabapple features Vice Steak Bar, Hyde Brewing, Smash Burgers by Vice and Yum! Thai on its website.
  • Crabapple Market's dining directory lists Olde Blind Dog, Six Bridges Brewing, Lily Sushi Bar, Resto L'Antoinette, Knuckies Hoagies, Peace Love and Pizza, The Nest Café and B&B Tavern Crabapple.

Market District Crabapple is one of the two truck sites. On Wanderlust nights, part of its parking area holds the trucks while its restaurants are a few steps away.

The changes on the edges of town, and their dates

Two other City projects have dates inside this same five weeks. Neither is a holiday event, but both affect how you get to downtown or what Milton will have nearby.

Thursday, November 5. Appen Media reports that crews are staining the stamped concrete at the Hopewell-Thompson and Hopewell-Bethany Bend roundabouts from about 9 a.m. to 4 p.m. Expect delays, but neither roundabout is closing fully. The work is part of Milton's Safety in Action initiative, paid for with a $1 million federal Safe Streets for All grant. The City plans to assess how these changes work before it considers similar ones elsewhere.

Late November into December 1. The City is doing due diligence on the 51.32-acre former Verizon campus in South Deerfield. City Council approved a purchase agreement in late September for the site as a possible "public anchor" for the area's redevelopment. Surveyors are studying the land's topography, the utilities underneath, and the location and extent of wetlands. They are also looking at what the site could offer for outdoor recreation, trails and public space. The City says no final use has been decided. Due diligence is expected to wrap up in late November. Milton will then either go ahead or use its right under the agreement to withdraw. If it goes ahead, closing could happen on or before December 1, per the City's October 21 update.

That puts the Deerfield decision in the week before the December 3 truck night, just as downtown Crabapple heads into its busiest stretch of the season.

If you own a home near downtown Crabapple, all this new weeknight activity is one reason to look again at what your address is worth. Julia Sosa-Rocha and our team follow Milton block by block, including what the City is planning for Deerfield, and we offer service in English and Russian. Request Your Free Home Valuation, and we'll put together a figure based on recent Milton sales before the December dates arrive.

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