This Holiday Season, Some of Wellesley Square's Best Shopping Is Only Passing Through

Two of the best-known storefronts on Washington Street have holiday tenants this year that won't be there next season. At 595 Washington St., the former Dover Saddlery is full of cashmere until Dec. 22. Just up the block at 579, the space E.A. Davis held for 120 years is now a bank branch. Inside it, a children's clothing brand that sold only online until this fall has a shop for the holidays.

That pattern runs through the whole season. Pop-ups, a rent-free retail program and a one-day market cover a large share of this year's gift shopping. Meanwhile the Square's permanent lineup is in turnover, and its biggest retail block is waiting on a timeline measured in years. If you know which spaces are temporary, you can see where the season actually happens and plan around it.

Two storefronts with an end date

The Cashmere Sale is back for its 16th year. As The Swellesley Report noted, it has moved through at least a half-dozen locations in town over the years. This season it's in the former Dover Saddlery, next to The Village Bank. Hours are Monday through Saturday, 10 a.m. to 5 p.m., and Sunday, noon to 4 p.m., through Tuesday, Dec. 22. There's meter parking out front and free parking in the back.

The Village Bank opened its first Wellesley branch on Sept. 16. It's a 4,300-square-foot space with a 24-hour ATM, and the old E.A. Davis sign and a cash register are on display in the storefront. A small retail area called the Village Shop sits inside. The bank works with a company called UpNext, which places small businesses there for four to six months each, rent-free. The same model is planned for future Village Shops in its Needham and Newtonville branches. More than 45 businesses applied, with ideas ranging from nonprofits to apothecary products to candy.

The first tenant, through the holiday season, is Piper&Cloth, Yvonne Piper's line of natural and sustainable children's clothing. She has sold online since 2022, so this is her first physical shop. In The Swellesley Report's preview of the branch, UpNext's Allison Yee explained the reasoning:

"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."

Shoppers get something out of that model too. Piper&Cloth is in the Square this December and may well be gone by spring. Whoever follows will be a business testing the same corner for the first time.

Why short stays fit the Square right now

Several longtime storefronts have gone dark this year. Wellesley Toy Shop at 59 Central St. closed after 32 years in business. Comina, the home decor shop at 566 Washington St., announced its closing in January, also after 32 years.

Comina and Panoply both sat in the Taylor Block, which Jumbo Capital now owns. By mid-October, brown paper and "for lease" signs were up in some of the block's empty windows. Rice Burg, Old School Pizzeria and Tutto Italiano are still operating there. At a Sept. 29 All Board Meeting, Wellesley Executive Director Meghan Jop said Jumbo is putting its redevelopment of 888 Worcester St. first. Because of that, she said, the company is unlikely to do much with the Taylor Block for five years.

One expected arrival has stalled. Wonder, the virtual food hall that has been opening along the East Coast, told The Swellesley Report over the summer that it planned to open in Wellesley next year, and it filed a building permit application in July for 56 Central St. In October it pulled its sign and construction applications from the Design Review Board, and no building permit has been issued. Orangetheory, which operates at that address, has told members that Wonder isn't coming and that it plans to keep building its Wellesley Square business. The Swellesley Report wrote that it wouldn't count Wonder out of finding another Wellesley space. The nearest Wonder for now is in Natick, where it opened in February.

A season with long-term plans on hold is exactly when businesses that can come in for a few months have an easier time finding room.

What's here to stay

The Square has added permanent tenants this year too. Most of them suit holiday errands better than holiday gifts.

Two more names belong on the list. SALT Patisserie, the Newton Centre bakery led by chef Thiago Silva, chose the former Starbucks at 68A Central St. for its second location. The Bra Shop announced plans for 22 Church St. in Church Square.

Put together, that's a coffee bar, a consignment shop, a restaurant, a bank and a gallery. Nothing on the permanent list replaces the toy shop or the home decor store that closed. For this season, the temporary tenants and one-day events fill that gap.

The biggest gift shop of the season is open for one day

The largest holiday shopping event in town isn't in the Square. Wellesley Marketplace 2026 takes over Wellesley High School, 50 Rice St., on Saturday, Nov. 21. Now in its 48th year, the Wellesley Hills Junior Women's Club market brings in more than 200 local businesses. There are indoor and outdoor food vendors and holiday raffle baskets. All proceeds fund scholarships and grants for the local community.

Two things are new this year: a shopper's lounge and a VVIP ticket. Here's how admission breaks down:

• VVIP, $50: 9 a.m. early entry, a reserved parking spot for the day, a special edition gift, swag bag and coupon flyer. Limited quantities.
• VIP, $30: 9 a.m. early entry, special edition gift, swag bag and coupon flyer. Limited quantities.
• Advance general admission, $15: entry from 10 a.m. to 4 p.m.

The reserved parking spot is the main difference between the two early-entry tiers. With 200-plus vendors at the high school for a single Saturday, that spot is what the extra $20 buys.

The calendar from here

The Massachusetts Horticultural Society's Festival of Trees has moved to a new opening day this year, Wednesday, Nov. 25. It's closed Thanksgiving and Christmas and has special vacation-week hours. The society says more than 18,000 guests come each season and that peak days and times sell out. Hot cocoa on arrival and s'mores at the firepits are included with a ticket.

Dec. 6 is the merchants' day

The permanent storefronts get their own day on Sunday, Dec. 6. That's when the Wellesley Square Merchants' Association runs its Holiday Stroll and Scavenger Hunt, 11 a.m. to 6 p.m. Each participating store puts up a snowflake sign. Players find it and get their card stamped or initialed by the shop. Each scavenger hunt site donates four $25 gift certificates or gift bags, dropped off at London Harness, 45 Central St. Merchants have until Nov. 20 to sign up, so the full list of stops will come together over the next week or so.

The Town Band's free Winter Concert starts at 3 p.m. that afternoon at the high school. You can do part of the stroll, drive over to Rice Street for the concert and still get back to the Square before the shops close at 6.

It's also the one day this season when the permanent Square gets the same attention as the pop-ups. The new gallery, the consignment shop and the long-running Taylor Block restaurants all fall within the stroll's footprint.

The Square itself is being redesigned. The Wellesley Square Improvement Project aims to finish a design that could go to Town Meeting for construction funding in 2027 or 2028. Its second public meeting, on the Central/Washington/Grove and Central/Crest/Railroad intersections, is expected sometime in November, with the date still to be set.

At The Shulkin Wilk Group, we follow Wellesley Square's storefronts, pop-ups and public meetings all year because they shape what living near the Square feels like. If a change on Central or Washington Street has you thinking about your own home's next chapter, we'd be glad to talk it through, discreetly and on your schedule.