"As a small business, you often feel unseen or overlooked or that the odds are against you, so this is really encouraging." Vernee Wilkinson said that to the Boston Herald in November 2010. She owned the Colorwheel Collection, a Roslindale shop that was just over a year old and sold children's clothing and handcrafted items.
The "this" was a new national idea. American Express and the National Trust for Historic Preservation had put a shopping day between Black Friday and Cyber Monday and called it Small Business Saturday. In Roslindale, that first year was tied to a neighborhood tree lighting, and the two have shared a Saturday ever since.
A Shopping Trip Timed to a Tree Lighting
According to the Herald's 2010 report, Mayor Thomas M. Menino signed a proclamation making Nov. 27 Small Business Saturday in Boston. New York's Mayor Michael Bloomberg had already done the same. Menino then "promised to back up his declaration with a shopping trip in Roslindale that coincides with the Roslindale Village Main Streets tree lighting on Saturday."
The tree lighting is the key detail. The mayor's Small Business Saturday visit was planned around a Roslindale Village Main Streets holiday event on the same day. Lucy Warsh, then a spokeswoman for Boston's Department of Neighborhood Development, told the Herald the visit was "a unique opportunity to highlight his support for small businesses on a national stage."
The national campaign and the tree lighting shared that Saturday in 2010, and the pairing stuck.
How the Story Grew Over Sixteen Years
By 2012 the Roslindale version had become an occasion of its own. Boston.com reported that year that the Village was getting ready for Small Business Saturday with its tree lighting and shop event. Karen Mills, then administrator of the U.S. Small Business Administration, was expected to attend. The same report said American Express created the holiday and that the first one was celebrated in 2010.
Roslindale Village Main Street now tells the story with more ownership. Its Small Business Saturday page says the first one, in 2010, "took place right here." It also credits the creation of the holiday to American Express, working with Menino, the National Trust and RVMS itself. In October 2026, the Jamaica Plain Gazette wrote that the neighborhood "helped pilot the very first Small Business Saturday."
The 2010 Herald report places a mayor's Small Business Saturday shopping trip in Roslindale on the day of the RVMS tree lighting, in the holiday's first year.
The 2012 Shop List, Fourteen Years On
The 2012 Boston.com piece listed the Roslindale merchants taking part that year: Birch St. House & Garden, Centre Cuts Salon and Day Spa, Joanne Rossman and Boston Cheese Cellar. The list shows how much of that first circle is still selling gifts in the Village.
Boston Cheese Cellar is gone. Universal Hub reported in February 2020 that its owner planned to close at the end of that month. Two of the other names are still in business. Several newer shops have also become part of a holiday walk through the square.
| Shop | Address | What's on the shelves |
|---|---|---|
| Birch St. House & Garden | 760 South St. | Home and garden gifts, candles, jewelry, housewares, bath and body goods, toys, baby gifts, locally made and fair-trade items |
| Joanne Rossman | 6 Birch St. | Cards, antiques, local art, homemade jams |
| The Centerpiece Flower Shop | 44 Belgrade Ave. | Made-to-order flowers, holiday collections, plants, home-and-garden items, books |
| Russ & Mimi's | 16 Birch St. | Coffee, pastries, breakfast and lunch, wine, groceries, gift cards |
| Rozzie Bound Co-op Bookstore | Roslindale Village | Books |
Birch St. House & Garden was on the 2012 list, and today its stock runs from candles to baby gifts, with an emphasis on locally made and fair-trade goods. That makes it the most complete one-stop gift shop on the walk. CBS Boston has described Joanne Rossman's gift shop as selling everything from cards and antiques to local artwork and homemade jams. The shop on Birch Street lists autumn Saturday hours of 10 a.m. to 4 p.m. If you're shopping there on Nov. 28, plan to go before the afternoon events in Adams Park. The Centerpiece Flower Shop on Belgrade Avenue offers holiday collections along with its regular flowers. Russ & Mimi's sells gift cards, which works for the person on your list who would rather choose their own coffee and pastries. Rozzie Bound is a cooperative bookstore.
Hours change around the holidays, so check each shop's site before you go.
Saturday, Nov. 28, in Order
The first year paired the day with a tree lighting, and the 2026 version still does. The Gazette's October preview describes the day the same way. You shop the Village during the day, and the day ends with the annual tree lighting in Adams Park, with free hot cocoa, an ornament decorating station and photos with Santa.
Here's how the day fits together:
- Park once. RVMS points shoppers to two lots. The Taft Hill Terrace Municipal Parking Lot is free. The Lower Commuter Rail Lot off Belgrade Avenue is paid through the PayByPhone app. RVMS listed it at $2 for Small Business Saturday in 2024 and lists it at $4 for this year's Dec. 6 Holiday Market.
- Shop the morning. Birch Street, South Street and Belgrade Avenue are all on the walk from either lot. Shops with shorter Saturday hours, like Joanne Rossman's 10-to-4 schedule, are easier to reach before the park fills up.
- Carry a bingo card. RVMS runs Shop Small Bingo. You can download, screenshot, print or pick up a card. Complete one line of five squares across, down or diagonally, then email the card to enter a drawing for a $50 gift card. Each person gets one entry, and the deadline is Dec. 15. That gives you two and a half weeks after Small Business Saturday to finish a line.
- End in Adams Park. Last year's lighting ran from 3 to 5 p.m. on the Saturday after Thanksgiving. Mayor Michelle Wu helped light the tree, with music from Making Music Matters and JP Honk and a performance by City Ballet of Boston. The Reindog Costume Contest for dogs in holiday outfits started around 4:15 p.m.
The 2025 emcee was Glenn Williams. At its fifth annual gala on Oct. 29, 2026, at The Substation, RVMS honored Glenn and Janice Williams, and the night raised $88,172 for local programming and small-business support, according to the Jamaica Plain Gazette. The same organization that runs the tree lighting raises money for the storefronts around it, which is the 2010 pairing kept going for sixteen years.
The Weekends on Either Side
Small Business Saturday is the middle of three weekends for the Village.
The weekend before, on Saturday, Nov. 21, the RVMS farmers market holds its last outdoor session of the year in Adams Park, 9 a.m. to 1:30 p.m. One week later, the same park hosts the tree.
The weekend after, the holiday shopping moves indoors and spreads across the square. The RVMS Holiday Market is on Sunday, Dec. 6, from 3 to 7 p.m. There will be craft vendors, live music throughout, and the regular shops open nearby. Vendors will be set up in three places: inside the Emerald Society, on Birch Street Plaza, and on the Sophia's Grotto patio. Joanne Rossman at 6 Birch St. and Russ & Mimi's at 16 Birch St. share a street name with the plaza. The same two parking lots apply, with Taft Hill Terrace free and the Belgrade Avenue commuter lot at $4 by app.
In 2010, the Herald called Small Business Saturday "a cheap way to draw some attention to the little guy." Sixteen years later, the Village has three weekends of holiday shopping and events around Adams Park.
At Juan Real Estate Group, we see this every season from the listing side. The Saturdays when Roslindale Square fills up are the ones our photographers try to capture, because a buyer looking at a home near Birch Street is also deciding about that walk. If you're thinking about what your place near the Village is worth, or how to show it so the neighborhood comes through in the photos, let's connect. Book a free valuation or consultation.
