The sixth annual Arlington Heights Holiday Stroll is on Saturday, December 12. This Saturday, November 21, is the last day to sign up to help decorate for it. The Arlington Heights Community Association's Winter Window Painting takes registrations until the 21st. Its 62 guaranteed spots go first come, first served, and the paintings it produces become the backdrop of the stroll. The same morning, the Old Schwamb Mill opens its annual Craft Fair at 17 Mill Lane. That puts the start of the Heights holiday season on a single Saturday at the east end of the neighborhood. By the time anyone strings lights on Mass Ave, the windows already have their painters.
November 21 Has Two Things Going On
The Old Schwamb Mill Craft Fair runs from 10 a.m. to 4 p.m. on Saturday, November 21. The Mill bills it as a start to holiday shopping, with handmade goods from local artisans under one roof. The 2026 maker list mixes categories:
- Jewelry from Michael Bacon, Carol Gordenstein, Ginny Remedi-Brown and Angelique Swingle, who also brings lithograph prints
- Pottery and ceramics from Dana Cooperson, Merrill Frank and Teresa Deible's "Clayful Expressions"
- Textiles from Robin Bergman, Preeti Mehta, Janet Steele and Beverly Hinckley's Textileations
- Wood from Tim Rix, plus Nancy French's wood and wool items
- Candles and bath products from Nelly Kenney's Kenney Kandles, Becky Radway and Helen Ray
- Home goods from The Gallery@57
Window painting registration closes that same day. If you paint, or have a child who wants to, you can spend the morning at the Mill and still sign up in time, as long as the 62 spots have not already filled. Registration closes once every slot is taken, so it can shut before the 21st.
What Signing Up Gets You
The rules on the Arlington Chamber of Commerce event page are short. Here is the sequence from registration to finished window:
- Register by Saturday, November 21. The fee is $30. Arlington residents can enter, and so can anyone who attends a school in Arlington.
- Watch your email about a week after registration closes. Painters get a window assignment, a rules and information flyer, and a list of supplies and tips.
- Show up Saturday, December 5, between 9 a.m. and 1 p.m. If the weather is bad, the rain date is Sunday, December 6, during the same hours. Selected acrylic paints and brushes, covered by the $30 fee, are handed out that day.
- Paint a winter scene. The event page mentions snowmen, polar bears and people at winter play. You can work alone or with a friend or parent. Painters under 12 need an adult with them.
The windows belong to 27 businesses in the Heights, and the paintings stay up through mid-January. So the work done on one December morning decorates the business district for about six weeks.
The Arlington Heights Community Association is made up of Heights business owners, residents and nonprofits. It meets on the third Thursday morning of each month. Besides the Holiday Stroll and the Heights Spring Fling, it runs three seasonal window paintings a year. The Chamber page lists Janet O'Riordan as the contact for anyone who wants to attend a meeting, volunteer at an event or donate.
The Center Takes One Thursday Evening
Arlington Center's main holiday evening falls between the Mill fair and painting day. First Lights in Whittemore Park is Thursday, December 3, from 6 to 7:30 p.m. It takes place in Whittemore Park in front of the Jefferson Cutter House at 611 Massachusetts Avenue. The Chamber's listing includes music, hot cocoa and cookies, a visit from Santa, live ice sculpting and a chance to tour the Cyrus Dallin Art Museum. The page also has a registration link.
First Lights is a weeknight event of about 90 minutes, all in one park. The Heights events are spread over Saturdays and run along Mass Ave storefronts. Together they make the season easy to plan. The Center has the one evening on the 3rd, and the Heights has the 21st, the 5th and the 12th.
On a Center morning, Colette is a few doors away at 681 Mass Ave. The French bakery opened in early November. In a YourArlington "Eatington" review, Frederick Kalil reported that owner Nathalie Beddiar chose Arlington for its energy. She told him, "Families come in together and read their books across from the library." The same review reports that all of Colette's bakers are French, that flour and butter come from France, and that the coffee is from Atomic Coffee Roasters on the North Shore. Kalil also warns that the kouign-amann and the palmier are best early in the day. Colette is open Wednesday through Friday from 7:30 a.m. to 5 p.m. and Saturday and Sunday from 8 a.m. to 4 p.m. It is closed Monday and Tuesday, so it's open on the Thursday of First Lights, though it closes an hour before the event begins.
What Last Year's Stroll Looked Like
The 2026 Heights Holiday Stroll is set for Saturday, December 12, from 2 to 5 p.m. It is free and goes ahead rain or shine. The 2025 schedule shows how the afternoon usually goes. Last year the stroll featured more than 60 winter-themed windows in 25 storefronts, painted by Arlington residents, according to the YourArlington event listing. Its activities were spread among everyday Heights businesses, plus a parish choir and a local TV studio.
| 2025 time | What happened | Where |
|---|---|---|
| 2:00–4:30 p.m. | Touch-A-Truck, bean-bag and candy-cane toss games | Heights Bus Depot, 1389 Mass Ave |
| 2:00–4:30 p.m. | Gingerbread-person and snowman photo op | Classic Kitchen and Bath Showroom, 1321 Mass Ave |
| 2:00–4:30 p.m. | Selfies with Reggie the Goalie | Sports Etc., 1303 Mass Ave |
| 2:00–3:30 p.m. | Children's winter craft with Tonya Grifkin | Roasted Granola Café, 1346 Mass Ave |
| 3:00–4:30 p.m. | Photos with Santa | ACMi Studio, 85 Park Ave |
| 3:45–4:30 p.m. | Cello and violin by Denise Lotufo and Telden Lopes-Lotufo | Roasted Granola Café, 1346 Mass Ave |
| 4:00–4:30 p.m. | Margaret Moody Puppets, "Taking Turns" | Kumon Math and Reading Center, 1343 Mass Ave |
| 4:45–5:15 p.m. | Arlington High School Madrigal Singers and Park Avenue Congregational Church singers | Outside ACMi, 85 Park Ave |
| 5:00 p.m. | Tree lighting | Outside ACMi, 85 Park Ave |
In 2025, Arlington Fire and Police, Intelligent Labor and Moving, and Little Latch Landscaping co-hosted the Touch-A-Truck at the bus depot. Free parking was at Arlington Coal and Lumber, 41 Park Ave. Last year's layout stayed within a short walk. Most of it sat on the stretch of Mass Ave between about 1303 and 1389, with the evening ending around the corner on Park Ave.
Last year a kitchen showroom, a tutoring center and a sporting goods store hosted the photo ops, the puppets and the selfies, while the Roasted Granola Café held both the craft table and the string duo. So the stroll needs two kinds of volunteers. Businesses lend their rooms for the afternoon. Residents decorate the glass out front, and their window registration closes on the 21st.
The Season at a Glance
- Saturday, November 21: Old Schwamb Mill Craft Fair, 10 a.m. to 4 p.m., 17 Mill Lane. This is also the last day to register for window painting.
- Thursday, December 3: First Lights in Whittemore Park, 6 to 7:30 p.m., 611 Mass Ave.
- Saturday, December 5: Heights Winter Window Painting, 9 a.m. to 1 p.m. The rain date is Sunday, December 6.
- Saturday, December 12: Sixth annual Heights Holiday Stroll, 2 to 5 p.m., free, rain or shine.
- Through mid-January: Painted windows stay up in 27 Heights storefronts.
Carol and Owen Toland of The Toland Team work just down the road in Belmont and keep an eye on events like these in Arlington. If you'd like to talk about a home in the Heights or near Arlington Center, we're glad to share what we know about the neighborhood, and a free home valuation is always available.
