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Wellesley Square's Holiday Shopping Is Happening in Borrowed Storefronts This Year

Yvonne Piper started her children's clothing line, Piper&Cloth, online in 2022. She taught herself to sew. When she first heard she could open a pop-up inside a bank branch on Washington Street, she told The Swellesley Report that she didn't even know what a pop-up was. Piper&Cloth is now the first brand in that Church Square space. Piper said she planned to include a section of archive pieces from her early designs, and the shop is set to stay through the holidays.

Two doors down, Needham's Heidi Wells has set up The Cashmere Sale in a former saddlery. The Sale's 16th Wellesley season runs until December 22.

Wellesley Square's newest holiday shopping this year sits in temporary arrangements on the Church Square block. Across Central Street, the Taylor Block's empty storefronts and the Square's streets are on schedules that run for years.

Two former anchors, two short-term tenants

The Village Bank opened its first Wellesley branch on September 16 at 579 Washington St. E.A. Davis sold from that address for 120 years. The bank kept a few reminders. The old E.A. Davis sign and a cash register are displayed in the storefront, and historical photos hang on the walls of the 4,300-square-foot space.

Inside the branch is The Village Shop, a rotating retail space that now lists itself as open in Church Square. Piper&Cloth is its first brand. The bank found its tenants through a company called UpNext. Each business stays four to six months, rent-free, and more than 45 have applied. Their ideas range from nonprofits and apothecary products to home goods and candy, according to The Swellesley Report. UpNext's Allison Yee explained the appeal of the model to the outlet:

"There's a lot that goes into launching a retail shop, and if you have to make long-term commitments and major dollar investments up front before you really get proof of concept, it's not the best way to go about it. That's where pop-ups come in."

When Piper&Cloth's run ends after the holidays, another business takes the space. When The Swellesley Report first covered the bank's plans, it wrote that Wellesley was seeing more chains and fewer independent retailers across town. It said the Village Shop would give unique businesses a chance to shine.

Next door at 595 Washington St., The Cashmere Sale has taken over the former Dover Saddlery. Over the years, the Sale has popped up in at least half a dozen different spots around town. This season's details:

  • Dates: Friday, October 16 through Tuesday, December 22
  • Hours: Monday to Saturday, 10 a.m. to 5 p.m.; Sunday, noon to 4 p.m.
  • Parking: Meters out front, free parking in back

So on one short stretch of Washington Street, two buildings that housed long-running retailers now host shops with an end date. Both are open now, and both are built around the holiday season.

Across Central Street, a longer clock

Jumbo Capital owns the Taylor Block, where Rice Burg, Old School Pizzeria and Tutto Italiano are still open. Brown paper and "for lease" signs cover some of the empty windows. Those were the spaces of Comina and Panoply, which have both left. Comina, a home decor shop, closed after 32 years in Wellesley Square.

Wellesley Executive Director Meghan Jop said at the September 29 All Board Meeting that Jumbo is focused first on redeveloping 888 Worcester St. Because of that, she said, it is unlikely to do much with the Taylor Block for five years. At the town's October 14 forum on the Square, The Swellesley Report heard that Jumbo will wait to see how the Wellesley Square plan turns out.

At 56 Central St., a July building permit application had suggested Wonder, the virtual food hall, was coming. Wonder has since withdrawn its sign and minor construction applications before a Design Review Board discussion, and the town has not issued a building permit. Orangetheory already operates at 56 Central. It has told members it is committed to building its business in Wellesley Square.

SALT Patisserie, the Newton Centre bakery led by chef Thiago Silva, has announced a second location at 68A Central St., in the former Starbucks space. The ownership group says it has turned down private equity buyout offers so it can expand on its own.

The streets themselves are still in design

The pop-ups sit next to the intersection the town is studying most closely. According to The Swellesley Report's account of the October 14 workshop at Hunnewell Elementary, attendees asked about pedestrians crossing Washington Street between the church and Anderson's Jewelers, at the five-way intersection. They also asked whether public space near the post office could be better used. Just over 30 people came, and more than a hundred had filled out the town survey by mid-October. Common themes were keeping parking, making the main intersections safer, and adding outdoor places to sit, such as sidewalk space or parklets.

The Wellesley Square Improvement Project covers Central and Washington Streets from Weston Road to Wellesley Avenue, plus parts of Weston Road, Crest Road and Grove Street, and all of Church Street. Construction funding is projected at about $6 million. The town expects to request it at Town Meeting in 2027 or 2028.

Here is how the different timelines in the Square compare:

Address or project What's there now Timeline
595 Washington St. The Cashmere Sale Through December 22
579 Washington St., The Village Shop Piper&Cloth Through the holidays; later tenants stay four to six months
Taylor Block Rice Burg, Old School Pizzeria, Tutto Italiano, plus papered vacancies Little change expected for about five years, per Jop
Square Improvement Project Design phase Funding request in 2027 or 2028

Public Meeting #2 is listed for November 18. It will focus on the layout of two key intersections, Central/Washington/Grove and Central/Crest/Railroad, along with traffic flow and pedestrian safety. Meeting #3, on the preferred design concept, is set for January 20, 2027. Anyone who wants a say in how they'll cross Washington Street in Church Square can join the November session. It comes a week before Thanksgiving, while the pop-ups are in their busiest stretch.

The holiday calendar around the Square

Saturday, November 21: Wellesley Marketplace. The Wellesley Hills Junior Women's Club brings more than 200 local entrepreneurs and artisans to Wellesley High School, 50 Rice St. VIP early entry starts at 9 a.m., and general admission runs 10 a.m. to 4 p.m. Expect food trucks and holiday raffle baskets. Proceeds go to local college scholarships and community grants. Tickets are on the club's site.

Sunday, December 6: Holiday Stroll and Scavenger Hunt. The Wellesley Square Merchants' Association runs the Stroll from 11 a.m. to 6 p.m. Players look for a snowflake sign in each participating shop and get their playing cards stamped or initialed. Each scavenger hunt shop donates four $25 gift certificates or gift bags, which are collected at London Harness, 45 Central St. Shop owners have until November 20 to sign up.

Through December 22: The Cashmere Sale at 595 Washington St. The Village Shop is next door at 579 Washington St., where Piper&Cloth stays through the holidays.

If you walk the Stroll on December 6, put Church Square on your route. The Cashmere Sale has just over two weeks left by then, and once Piper&Cloth's holiday run ends, a different business moves into the Village Shop.

If you own a home near Wellesley Square and are wondering how the improvement project or a changing storefront mix might affect your plans, Colleen Kelly Homes is glad to talk it through, one block at a time. Schedule a free strategy call.

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