Arlington's Holiday Windows Are Painted by Neighbors, and Signups Close Saturday

On Saturday, Dec. 12, from 2 to 5 p.m., the sixth annual Heights Holiday Stroll runs along Massachusetts Avenue in Arlington Heights. It is free and goes ahead rain or shine. Walk it that afternoon and you will see storefront windows covered in snowmen, polar bears and people at winter play. Those windows are painted by residents, by anyone who attends school in Arlington, and by parents working beside their kids, all in a single four-hour session the Saturday before.

Registration to paint one of those windows closes this Saturday, Nov. 21. That is three weeks before the Stroll and well before most households have hung a single light. Arlington's holiday season shows up on the calendar as a December run from the Center to the Heights. In practice it starts this weekend, and the most hands-on part of it is limited to whoever registers in time.

Saturday, Nov. 21: a craft fair and a deadline

The first holiday event of the year and the first deadline land on the same day.

The Old Schwamb Mill holds its annual Craft Fair on Saturday, Nov. 21, from 10 a.m. to 4 p.m., and the Mill bills it as the place to start your holiday shopping. The Mill's 2026 list names 24 artisans. Among them:

• Nelly Kenney's Kenney Kandles
• Teresa Deible's "Clayful Expressions" ceramics, along with pottery from Dana Cooperson and Merrill Frank
• Wood items from Tim Rix, and wood and wool upcycled pieces from Nancy French
• Paintings from Nidhi Jha
• Jewelry and lithograph prints from Angelique Swingle
• Home goods from The Gallery@57

The rest of the roster covers textiles, photography, cards and paper crafts, and bath products. That makes it a good place to buy for a lot of names on one list in a single trip.

The window-painting deadline is the one that's easy to miss. The Arlington Heights Winter Window Painting runs on a short list of rules, and each one affects whether you get a window:

• Deadline: Saturday, Nov. 21. The registration site also closes as soon as every slot is taken, so it can close before then.
• Capacity: Space is guaranteed to the first 62 entries, first come, first served.
• Windows: Designated storefronts at 27 Heights businesses.
• Cost: $30, which covers an assortment of acrylic paints and brushes handed out on painting day.
• Who can paint: Arlington residents and anyone who attends school in Arlington. Painters under 12 need an adult with them.
• What comes next: About a week after registration closes, painters get an email with their window assignment, a rules sheet and a list of supplies and tips.

Painting happens Saturday, Dec. 5, from 9 a.m. to 1 p.m., with a rain date of Sunday, Dec. 6, during the same hours. The paintings stay up through mid-January, so a window painted that morning is part of the Stroll a week later and is still there after New Year's.

Who builds the Heights' December

The painting and the Stroll come from the same small group. The Arlington Heights Community Association organizes the window painting with the Arlington Chamber of Commerce. The association describes itself as Heights business owners, residents and nonprofits who meet monthly on local issues, beautification projects and public events. It runs three seasonal window paintings a year, plus the Heights Spring Fling and the Heights Holiday Stroll.

Its meetings are on the third Thursday morning of each month. This month that is today, Nov. 19, two days before the painting deadline. Anyone who wants to attend, volunteer or donate can reach Janet O'Riordan, who is also the contact listed for the Stroll.

So the Heights windows are painted by neighbors, and the same group of Heights business owners and residents sets up the painting, the Stroll and the rest of the neighborhood's events through the year.

The four weeks in order

Once the Nov. 21 deadline passes, everything else is about turning up. The season moves from Arlington Center to the Heights over three Saturdays and two weeknights:

Dec. 3 and Dec. 8 in the Center

First Lights in Whittemore Park is a weeknight event, Thursday, Dec. 3, from 6 to 7:30 p.m. It takes place in front of the Jefferson Cutter House. The Arlington Chamber of Commerce and the Cyrus Dallin Art Museum list music, hot cocoa and cookies, a visit from Santa, live ice sculpting and a chance to tour the Dallin museum. Since it runs for 90 minutes on a school night, families can get there after dinner and still be home at a reasonable hour.

Five days later, the Center for Jewish Life Arlington-Belmont holds a Chanukah Gelt Drop at the Arlington Fire Station, 411 Massachusetts Ave., at 4 p.m. on Tuesday, Dec. 8. The center's page asks people to say whether they plan to attend and how many adults and children are coming.

The new stops near Whittemore Park

Two places opened this fall within easy reach of the Center events.

Colette Bakery opened at 681 Massachusetts Ave., in the space that was Symmes Mini-Mart until it closed a couple of years ago. Boston Restaurant Talk reported that it joins the bakery's locations in Boston's South End, Melrose and Medford. In a review for YourArlington, Frederick Kalil wrote that the bakers are French, the flour is stone-ground Grands Moulins de Paris, the butter comes from Normandy, and the coffee is from Atomic Coffee Roasters. Owner Nathalie Beddiar told him why she picked Arlington:

"We liked the energy. People ride bicycles and enjoy being outside. Families come in together and read their books across from the library."

The same review says Beddiar intentionally avoids offering wifi and that the best-selling item is the croissant au chocolat, which the pastry case labels the Cho-Colette.

The hours affect the holiday dates. Colette is open Wednesday through Friday from 7:30 a.m. to 5 p.m., Saturday and Sunday from 8 a.m. to 4 p.m., and closed Monday and Tuesday. On First Lights night it closes an hour before the park event begins. It is closed on the day of the Gelt Drop. On Stroll day it closes at 4, an hour before the Heights windows wrap up. And on Nov. 21, Kalil's tip that the cases are fullest early in the morning makes it a good first stop before the Mill opens at 10.

Fresh & Go!, at 325 Broadway in Arlington Center, keeps the opposite schedule. Patch reported on Nov. 6 that this is the company's first location open 24 hours a day. Run by Arsenal Catering Group, it sells food from refrigerated smart coolers. You tap a card, open the door, take what you want and walk out, and AI item recognition charges you without a cashier. Food is prepared daily at the group's commercial kitchen in Cambridge. The menu includes bacon, egg and cheese bagels, smoked salmon bagels, caprese sandwiches and vegan falafel wraps, along with canned Starbucks coffee and Nantucket Nectars. For a 7:30 p.m. exit from Whittemore Park or a Tuesday when Colette is closed, it's the place in the Center that is always open.

Saturday's order of operations

The deadline is the one item on this list that can't be made up later. If you want to spend Dec. 5 painting a polar bear on a Heights storefront, register before Saturday ends or before the 62 guaranteed spots fill, whichever comes first. You can then spend the rest of the day buying gifts from the two dozen makers at the Old Schwamb Mill.

If you're planning a move around the school calendar or the holidays and want to know how Arlington's December rhythm fits the timing, Martha Sevigny is glad to talk it through over a croissant and coffee in the Center. Schedule a confidential consultation whenever it suits you.