Tucked behind towering boxes of toys and holiday decorations, Melissa Scammell works away each week in the back of her Vineyard Haven store, Rainy Day. She orders merchandise, designs the shop’s ever-changing window displays and, lately, with Christmas approaching, untangles string lights and unwraps delicate ornaments.

“Our Christmas trees will be arriving at the store next week,” said Ms. Scammell. “We always try to do a lot of events and displays around the holidays. It’s one of our busiest times.”

But this year, the holiday season brings with it an added gift — Rainy Day is celebrating its 50th anniversary, a milestone that Ms. Scammell said feels surreal.

The Vineyard Haven business started in 1974. A new location in Edgartown opened in recent years. — Zivah Solomon

“Way back, this building actually used to be the post office,” she said. “It’s so fun when people come in and they remember that... and the changes that the building and store has gone through over the years.”

Since opening in 1974, Rainy Day has had many owners. Ann Milstein and her husband Frank Piccione started the store and ran it for three decades, establishing it as a year-round Main street staple for kitchen goods and Island-made novelties.

The couple sold Rainy Day in 2003 to Heather Kochin, who expanded its product selection to include home decor and children’s toys and games.

Ms. Scammell and her husband Bob joined the Rainy Day team as business partners with Ms. Kochin in 2014. At the time, the two were summer residents looking to transition to the Island full time and engage more with the Vineyard’s off-season community. Four years later, they became official year-rounders and took over sole-ownership of the store.

“We’d been shopping [at Rainy Day] for a long time,” said Ms. Scammell.

Something for every occasion. — Zivah Solomon

“We really wanted to be a part of something, you know, embedded in the community year round,” added Mr. Scammell. “It’s an opportunity to give back and provide employment for people all year.”

At first, taking over such a well-known Island business felt daunting, said Ms. Scammell. But it didn’t take long for the couple to find their groove.

Charmed by the store’s long-time look and products, the Scammells decided to keep Rainy Day’s customer-facing side mostly the same. Instead, they have focused their five years of ownership on improving the business’ online services and expanding the Rainy Day experience to Edgartown.

“We really didn’t want the place to fail on our watch,” Ms. Scammell said. “There’s just so much history here. But I’m proud to say we’ve been able to continue on and grow. We opened a second store in Edgartown, grew our online presence and even navigated through Covid.”

Managing both stores is demanding, and soon Mr. Scammell will retire from his primary job as a chemical engineer to dedicate more time to Rainy Day. But even in the thick of summertime or holiday season chaos, the shop continues to provide the Scammells a priceless present: connection to their community.

50 days of discounts to celebrate 50 years in business. — Zivah Solomon

“It’s amazing how much support we get all year round from both tourists and residents,” said Mr. Scammell. “People love to shop small and shop local, and we really get to know everyone.”

To celebrate its 50th anniversary, Rainy Day is having daily special promotions through Dec. 24, including a drawing on the final day for a $500 gift card.

“We thought it would be really fun to do discounts for the 50 days prior to Christmas for our 50 years,” said Ms. Scammell. “So now is the time to shop... and to just come in and give us a visit.”