"For many of our small businesses, this season carries them into the new year." That line comes from Fabulous Hillcrest's Shop Hillcrest for the Holidays page, and it explains more about Hillcrest's December than any event listing does.
Hillcrest doesn't have one big tree lighting. Its season is a chain of programs run by the Hillcrest Business Association, and they work together. Purchases earn raffle entries. The raffle pays in gift certificates you can only spend at Hillcrest businesses next year. The biggest holiday event pours its drinks inside retail shops. Once you know how the pieces connect, it's easier to decide where your evenings, and your gift budget, go between now and Christmas Eve.
A raffle whose prize is a 2027 shopping spree
Shop Hillcrest for the Holidays runs from Saturday, November 28, through Thursday, December 24, 2026. From Small Business Saturday through Christmas Eve, every purchase at a participating Hillcrest business earns an entry into a raffle for gift certificates from local shops, restaurants and services. The association describes the prize pool as reaching "thousands of dollars."
Entering takes about a minute. Participating businesses put a "Shop Here" poster in the window. At checkout, you scan the QR code on the Shop Hillcrest table tent and fill in your name, email, purchase date and the business you bought from. Each purchase earns another entry.
The payout is what makes this raffle different. Winners don't get cash. They get credit to spend in the neighborhood throughout 2027, which the page calls "a 2027 shopping spree in the neighborhood." So a purchase made this December brings in a second round of business for the same shops next year.
Two days count double:
- Small Business Saturday, November 28: each raffle entry counts as two.
- Taste 'N' Tinis, December 10: purchases made during the event also earn double entries.
The participating businesses for 2026 haven't been posted yet. The page tells shoppers to check back for the list.
Taste 'N' Tinis pours its drinks inside the shops
The second double-entry day is the season's biggest single night. Hillcrest Taste 'N' Tinis runs Thursday, December 10, 2026, from 5:30 to 9 p.m. It's a 21+ sip-and-stroll through the Hillcrest LGBTQ+ Cultural District.
What sets it apart is who pours. Restaurants serve signature bites and desserts, and neighborhood retail shops pour the mini martinis and holiday cocktails. Your ticket includes a passport good for one Mini Tini at each participating retail location and one seasonal bite at each participating restaurant. Participating shops tie red and white balloons to their doors. Because the drinks are in the stores, you're browsing the racks between sips, and anything you buy there earns double raffle entries.
The 2026 basics:
- General admission starts at 5:30 p.m. and comes with a plastic commemorative mini martini cup.
- VIP starts at 5 p.m. and comes with a commemorative 2026 Mini Martini Glass. Availability is limited.
- Check-in happens at two will-call locations, one on each end of the neighborhood, where you pick up your passport, map and tasting glass. Bring a valid ID.
- Tickets aren't on sale yet. Fabulous Hillcrest's newsletter gets early access before they go public.
Last year's numbers give a sense of scale. The association's November 2025 press release said the event usually draws nearly 1,000 attendees and listed the east side will-call at 1601 University Ave. KPBS's listing for the December 11, 2025 event counted more than 20 participating locations, with tickets at $30 to $40. 2026 prices haven't been announced.
The 2026 route isn't published either, but the past lists show which stops keep coming back. Ace Hardware, The Unoptical, Village Hat Shop, Gioia's Room, Green Fresh Florals, Crest Cafe, Urban Mo's and Humanity all appear in both 2019 and 2024. The 2024 list also included Buffalo Exchange, Babycakes, Baja Betty's, Hillcrest Brewing Company, Gossip Grill, Cork & Stem, Divo Diva, NOLA on 5th, Oates General, Kava Collective, Fruit Craft, Flicks and Secret Barbershop. A hardware store pouring holiday martinis is about as Hillcrest as a holiday tradition gets. So far, one 2026 perk has been announced: The Unoptical says it will hand out surprise giveaways during the event.
From December 1 through 12, the shops supply the prizes
Shop Hillcrest's page also links to a partner guide for 12 Days of Fabulous, a run of daily Instagram giveaways on @fabuloushillcrest. Each day features a different local business, and the number of gifts matches the date. The December 1 winner gets one gift, and the December 12 winner gets twelve.
Businesses donate the prizes, and the association runs the giveaway. Posts go live at 9 a.m., entries close at 11:59 p.m. Pacific, and a random eligible winner is chosen, confirmed to follow both accounts, and announced the next day. Businesses have until November 13 to sign up, and the lineup is confirmed November 18. The twelve featured shops should be known by late November.
Shops donate prizes in early December. Shops host the tastings on December 10. Shoppers who buy from those shops earn credit that comes back to the same storefronts in 2027.
The November night that sends its money outward
One event in the season works differently. Festival of Trees takes place at Rich's San Diego on Sunday, November 22. VIP entry starts at 4 p.m., the main event runs from 5 to 8 p.m., and it's 21+. The ticket page on Universe lists prices from $56.10 to $509.95.
The Festival of Trees is sponsored by BGCA/Big Gay California, a 501(c)(3) nonprofit. Professionally decorated artificial trees are raffled and auctioned, then delivered to winners' homes anywhere in San Diego County. Organizers say 100% of proceeds benefit the San Diego LGBTQ+ community. Here's how the totals have moved:
| Year | Raised |
|---|---|
| 2021 | Just under $23,000 |
| 2022 | $40,000 |
| 2023 | $46,000 |
| 2024 | $66,000 |
| 2025 | $52,500 |
Organizers say that money has gone to HIV/AIDS services and LGBTQ+ mental health and suicide prevention in San Diego. The 2026 beneficiaries haven't been named yet. The Word San Diego's November 2025 feature put the event's total since it began at more than $179,000.
Six days earlier, on Monday, November 16, from 5 to 9 p.m., the 4th Annual Hillcrest Honors celebrates the people, organizations, businesses and events behind the neighborhood. Rick Cervantes and Benny Cartwright founded it in 2022 through the @HillcrestSanDiego Instagram account. Honorees are picked by a selection committee from public nominations, judged on community impact. The categories cover the whole neighborhood economy, from Fabulous Bar and Bartender to Restaurant/Cafe and Hillcrest Service Industry All-Star. The venue hasn't been announced, so check the official Hillcrest Honors page before you go.
Sunday mornings and two new stops for the route
The Hillcrest Farmers Market keeps its usual hours all season. It runs every Sunday, 9 a.m. to 2 p.m., on University Avenue between Herbert Street and Park Boulevard, with the address listed as 1601 University Ave. The association's calendar lists dates on November 1, 8, 15, 22 and 29 and December 6, and says the market has more than 175 vendors selling produce, gifts, crafts, flowers and clothing. That makes the November 29 market, the day after Small Business Saturday, an easy second stop for gift shopping.
The University Avenue site is still a temporary home while the Normal Street promenade is built. In July 2026, KPBS reported that the promenade's underground work was done and that officials expected the project to be finished by the end of 2026. Our August post explains why the market's move back to Normal Street kept slipping.
Two places that opened this summer won't show up on any past Taste 'N' Tinis list. Eater San Diego reports that Mr. Charlie's opened July 11 at 3896 Fifth Ave. Axios San Diego reports that Pali Wine soft-opened August 12 in the space Cellar Hand left after closing July 19. The Perr family, who own Pali Wines, ran both.
The season in order:
- Sunday, November 1, 8, 15, 22, 29 and December 6: Hillcrest Farmers Market, 9 a.m. to 2 p.m., 1601 University Ave.
- Monday, November 16: 4th Annual Hillcrest Honors, 5 to 9 p.m.
- Sunday, November 22: Festival of Trees at Rich's San Diego, VIP at 4 p.m., event 5 to 8 p.m., 21+.
- Saturday, November 28: Small Business Saturday and the start of the Shop Hillcrest raffle, with double entries.
- Tuesday, December 1 through Saturday, December 12: 12 Days of Fabulous on @fabuloushillcrest.
- Thursday, December 10: Taste 'N' Tinis, 5:30 to 9 p.m., VIP from 5 p.m., 21+, with double entries.
- Thursday, December 24: Last day to earn raffle entries.
At Emerson Group, we track Hillcrest's storefronts as closely as its rents, because a commercial district that recycles its own holiday spending is part of what keeps a neighborhood holding its value. If you own property near University Avenue or Fifth Avenue and want to talk about how the neighborhood's business corridor fits into your hold, sale or 1031 plans, schedule a Wealth Call with our team.
