"I have been renting my current location for over 10 years and I have outgrown the space," Cloverdale massage therapist Stephanie Reitzell told the North Bay Business Journal this summer. She was describing a 400-square-foot suite at 126 N. Cloverdale Blvd. Her new space is a few blocks south at 119 S. Cloverdale Blvd., in the building that was the Kelley & Young tasting room for years. When the Cloverdale Wine Walk started its new season this month, the organizers made that address their headline check-in.
The detail matters more than it seems. On first Saturdays, Cloverdale runs a wine event whose front desks are a spa and an optical shop. The wineries come in as guests of downtown storefronts. If you want to know how the boulevard gets through winter, that arrangement is the clearest view you'll get.
From Pouring Room to Front Desk
Kelley & Young started in 2005 as Kathleen and Jim Young's label, made from grapes grown on the Young family's Geyserville land. On December 18, the winery announced that its 1,332-square-foot room at 119 S. Cloverdale Blvd. would go to appointment-only visits at the start of 2026. A Kelley & Young representative later said the winery is looking for a new tasting room location. Reitzell bought the building on May 15 and said she planned to use it to expand Tranquility Massage & Spa.
Kelley & Young was a Wine Walk participant for years. Its own event listing for the February 1, 2025 walk described that season as the event's "third year." Now the official Wine Walk page lists "Tranquility Massage & Spa – 119 S. Cloverdale Blvd (formerly Kelley & Young Tasting Room)" as the new check-in. So the room still serves the event. The job has changed from pouring wine to handing out wristbands.
A Wine Event Run by the Shops
The walk is organized as "a collaboration of numerous businesses in Downtown Cloverdale that will host wineries, breweries, pop-up vendors and live music." The hosts and pourers change from month to month. The second check-in is I.SEE. Optical Company at 210 N. Cloverdale Blvd. With one desk at each end of the boulevard, you can start the walk from whichever end is closer to where you parked or live.
Here's how a walk Saturday works, according to the organizer's page:
- Buy ahead or at the door. The $45 Early Bird Standard Ticket is sold online only and closes at midnight on the Thursday before each walk. On the day, the price goes up to $50.
- Know what the ticket covers. A standard ticket includes wine tasting at each participating stop, olive oil and/or cheese tastings, and a lunch special. The $30 Designated Driver Ticket covers the olive oil and/or cheese tastings plus the lunch special.
- Bring only your ID. Buying a ticket puts you on the check-in list.
- Check in before 1 p.m. The organizers say this cutoff comes from the event's ABC permit, so arriving late in the afternoon won't get you in.
The Cloverdale Chamber of Commerce calendar lists walks from 11 a.m. to 3 p.m. With a 1 p.m. cutoff, the real window to start is the two hours before lunch.
Next Door at 117
On the same block, just one number down from the new check-in, is a business that has been through its own reopening this year. Pick's Roadside reopened at 117 S. Cloverdale Blvd. on Saturday, January 10, 2026. The new owner, Anidel Hospitality, is led by Chris Fanini and bought and renovated the old roadside stand. Sonoma Magazine reported a menu built around burgers, shakes and root beer, with Wagyu beef, wine and beer alongside the classics.
The hours have changed since that January report. Pick's own site now lists noon to 6 p.m. daily, which is different from the winter schedule Sonoma Magazine printed at the reopening. Pick's online ordering page on Toast was taking scheduled orders as of this week. On a walk Saturday, those posted hours mean Pick's opens about an hour after the walk does and keeps serving for three hours after it ends.
The north end of the boulevard has been moving too. North End, the women's clothing and accessories boutique owned by Bri Bohanan and Mollie Asay, moved into a larger space at 233 N. Cloverdale Blvd. in January. So both ends of downtown have spent 2026 rearranging into bigger or different rooms, and the Wine Walk route runs through all of it.
Why This Calendar Runs While the River Towns Slow Down
The Wine Walk runs on a reverse schedule, and it has for several years. A City of Cloverdale newsletter listed the 2024–25 season as October 2024 through May 2025, with a walk on November 2, 2024. The Chamber listed the 2025–26 season as October 2025 through May 2026. The current season runs first Saturdays from October 2026 through May 2027. None of the published materials say why the organizers chose October through May. What they do show is that the walk begins after Friday Night Live ends for the summer and stops before it comes back.
The first walk of the season was October 3. The rest of fall in downtown Cloverdale stacks up like this:
| Date | Event | Where | Details |
|---|---|---|---|
| Sat., Oct. 17 | Open Mic Night | Cloverdale Performing Arts Center | 7–9 p.m. |
| Oct. 23–25 | Cloverdale Cabaret – Halloween Special | Cloverdale Performing Arts Center | 7 p.m. nightly |
| Fri., Oct. 30 | Downtown Trick-or-Treat | Downtown | 4–6 p.m., Chamber event |
| Sat., Nov. 7 | Cloverdale Wine Walk | Check-in at 119 S. or 210 N. Cloverdale Blvd. | 11 a.m.–3 p.m. |
| Nov. 13–22 | The Business of Murder | Cloverdale Performing Arts Center | Nov. 13, 14, 15, 20, 21, 22 |
| Sat., Dec. 5 | Cloverdale Wine Walk | Check-in at 119 S. or 210 N. Cloverdale Blvd. | 11 a.m.–3 p.m. |
| Dec. 11–13 | Winnie-The Pooh A Christmas Tail | Cloverdale Performing Arts Center | Three-day run |
Most of the season happens indoors and within a few blocks: the Performing Arts Center stage, the Chamber's afternoon in the street, and two Saturdays of storefront tastings. Only the Wine Walk asks you to buy ahead, and the early-bird price for the November 7 walk ends at midnight on Thursday, November 5.
What Hasn't Been Announced
The organizers haven't published the pourers for November or December yet. Neither the Wine Walk site nor the Chamber listing names the participating wineries, breweries or vendors for this season's dates. Because the lineup changes every month, the November group will probably look different from October's.
Kelley & Young hasn't announced a new tasting room address. Its last public word, through a representative, was that it is still looking. No source gives the exact date Tranquility opened at 119 S. Cloverdale Blvd. The spa's booking site now lists that address and its massage and spa services. The town's December traditions haven't been confirmed for 2026 either. The holiday parade form on Cloverdale Main Street's site is still labeled 2025. Sonoma County Tourism's Winter Festival listing still shows last year's date, December 5, 2025.
Until those dates come out, the dates that are set are the first Saturdays: November 7 and December 5, with check-in at 119 S. or 210 N. Cloverdale Blvd. before 1 p.m.
The team at Continuum Real Estate keeps track of which Cloverdale storefronts change hands and what moves into them. If you'd like to talk about a building on the boulevard, or about how Cloverdale changes from season to season, we're glad to compare notes over a glass at the next walk.
This article is general information, not legal, tax or financial advice. Consult a qualified professional about your situation.
