Overview: Shop Hillcrest for the Holidays

Through Dec. 24, shoppers can visit participating business where they can fill out a raffle ticket to be entered into a draw to win a big shopping spree in Hillcrest.

With only one week somehow remaining until Christmas, some shoppers are likely beginning to panic about what to buy for the special people in their lives.

If that’s you, Hillcrest might be the perfect place to turn to. One week remains in the Shop Hillcrest for the Holidays event.

Through Dec. 24, shoppers can visit participating businesses where they can fill out a raffle ticket to be entered into a draw to win a big shopping spree in Hillcrest.

The more people shop, the more raffle tickets they can acquire, increasing their odds of winning. Shopping on Double Points Days means raffle tickets are counted twice.

The program is exciting for shoppers — but Hillcrest businesses also look forward to this time of year.

“Come enjoy the neighborhood and the experience of being a local and shopping local,” said Kris Nelson of Bluestocking Books. “Locals like the idea of winning gift certificates to the neighborhood they love so they can try places they haven’t been to yet, and can return to the ones they do know and enjoy. It’s fun!”

For Negociant Winery co-owner Morgan Ciani, this event has led to an exceptional holiday feeling in 2025.

“Compared to last holiday season, we’ve seen more people intentionally choosing to shop local and really engaging with the businesses here,” Ciani said.

“Guests are asking questions, taking their time, and looking for gifts that feel thoughtful and personal… that connection has made this season feel even more meaningful than last year.”

Ciani said that guests to the area should slow down and enjoy the experience.

“Hillcrest is full of unique, locally-owned shops where you can find gifts that actually tell a story…. Whether it’s a bottle of wine chosen for someone specific or a recommendation from someone who knows the product, those touches are what make holiday gifts special.”

Ciani said that makes a huge difference for small businesses in the of area.

“It brings consistent energy into the neighborhood, introduces us to new customers, and helps build long-term relationships beyond the holiday season,” Ciani said. “For us at the winery, it’s about welcoming people in, sharing our wines, and becoming part of their traditions.”

Crest Cafe’s Enrique Medina notes how walkable Hillcrest is, making it easier to visit countless businesses all in one day. 

“This season has been more engaging,” Medina said. “A lot more customers are filling out cards.

“There is so much to see,” he added. “This event helps because it gets people in the door. It brings new people to the area. This time of year is festive and fun.”

Oates General owner Brian Musial opened his shop two years ago, so technically, this is his third holiday as a Hillcrest retailer.

“The Shop Small promotion has definitely brought in some new customers, as did the Taste ‘n’ Tini’s event from a couple of weeks ago, also organized by Fabulous Hillcrest,” Musial said.” I’ve definitely had a few attendees from that event return in the following week to shop, as they wanted to spend more time in my store, which was wonderful.”

As Musial sees it, the variety of shops in Hillcrest is a solid draw for greater San Diego shoppers. 

“My storefront is adjacent to Footnotes Bookstore, a neighborhood institution of the past 35-ish years,” Musial said. “We’ve got great cafes with independent coffee roasters, unique apparel (new and used), bike shops — even a tennis shop.”

Plus, bringing in more money for the local economy is something Musial and many other Hillcrest small business owners can get solidly behind. 

“It truly is a ‘something for everyone’ business district,” said Musial. “And I’m proud to add to it.”

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