Cynthia Fillmore, owner of Windfall Gallery in Chestnut Hill, wants to clarify one important distinction: her business is moving, not closing. 

Fillmore put up window signs at the store’s original location (7944 Germantown Ave.) saying Windfall is moving up the Hill to its second location (8419 Germantown Ave.) However, not everyone seems to have read the signs.

“People are still coming in saying, ‘It’s a shame that you’re closing.’ We’re not closing,” Fillmore laughed.

Windfall’s history

Windfall, which first opened in 1984 under former owner Kay Baluarte, is filled with jewelry, clothes, and other handmade gifts from more than 200 different artists. Fillmore joined the team in 2007 after starting her career in television production. Once she became a stay-at-home mom, Fillmore said she needed a part-time job to get her out of the house.

In 2014, Baluarte retired from Windfall and sold the business to Fillmore. Both women received suggestions to move the store uphill, but it wasn’t until after the COVID-19 pandemic that Fillmore decided to take a risk and open the second location in October 2021. What was supposed to be a three-month pop-up shop quickly turned into a permanent stay.

However, after almost four years, Fillmore decided that running both shops became too much work. Windfall’s permanent relocation comes after Fillmore was forced to make a tough financial decision for the business.

“I was stretched so thin, trying to rob Peter to pay Paul to make both of these float,” Fillmore said. “I felt like the water was rising and I was drowning.”

Since keeping both locations was not sustainable, Fillmore had a difficult decision to make. She said she held on to the original location “a lot longer than I should have” because it carried sentimental value. 

Fillmore would regularly hear from customers who had been going to the store since they were children. However, the second store was under construction to expand its square footage. Plus, Fillmore said, the second location couldn’t be beat.

“It’s insane how foot traffic up here [at the second location] is just so different from down there [at the original location],” Fillmore said. “I felt like I was in a different town, truly. It’s less than half a mile. It’s four and a half blocks between my two locations and it literally feels like I’m in two different towns.”

Fillmore announced Windfall would be relocating uphill in early June, starting a 50% off sale at the same time to lessen the inventory needing to be moved.

Difficult decisions

Although the sale helped Fillmore unload plenty of items, consolidating two stores into one was still a demanding undertaking. She enlisted the help of Will Brown, owner of the Duke Barber Company next door to Windfall’s original location, as well as various family members and friends. 

In addition to the heavy lifting, Fillmore said one of the toughest aspects of moving stores was saying goodbye to three of her employees.

“That was heartbreaking,” Fillmore said. “It was another reason why I held on [to the original location] so much longer than I needed to, because I don’t want to let them go.”

A final difficult part of the move was informing Fillmore’s landlord, Bob Elfant of Elfant Pontz Properties. 

“It felt like I was breaking up with someone; it was horrible,” Fillmore said. “But he knew it needed to be done. I’m a horrible business decision person. I run on emotion and that’s not how you do business. But [Elfant] is awesome.”

A new chapter

Fillmore’s worrying turned out to be for naught. Elfant is already in talks with Brown to expand his barber shop into Windfall’s old space.

“I’ve been in business for 10 years here on the Hill at that location and I’ve never had the opportunity to expand here,” Brown said. “So I’m going to take Windfall’s space, increase my footprint, and create more opportunities for people to get upscale barbering.”

Brown said there is no set timeline for when expansion will be complete, but he is aiming for the fall. However, not having Fillmore right next door will be an adjustment.

“She’ll be missed. … Now I don’t have a neighbor to knock on the door and borrow a cup of sugar,” Brown joked. “I’m very happy for her and her move. … She’s one of my besties on the Hill.” 

Maggie Dougherty can be reached at Margaret@chestnuthilllocal.com.