The Chelsea Area Chamber of Commerce's 21st annual Wine, Walk, & Shop runs Friday and Saturday, November 6 and 7, and it has no single schedule. The Ann Arbor Observer's listing gives it as free admission. The Chamber's part is a free shopping bag, a map and a photo backdrop at the info booth, with the Chelsea DDA as the 2026 presenting sponsor. Everything else comes from about 40 separate listings, and each business sets its own price, hours and day.
Friday is mostly a day for store specials and dinner music. Saturday has four markets with different hours, all open at once for only a short stretch. Pick your day before you pick your shops.
A format that started inside one Main Street shop
The event ran under a different name until recently. Chelsea Update's preview of the 2025 edition called it the 20th annual Wine, Women and Shopping, set for November 7 and 8, with a free shopping bag, a coupon book and a photo booth. For 2026 the Chamber lists it as Wine, Walk, & Shop, still two days and still built around the free bag and the merchants' own offers.
Its roots explain why it still runs store by store. MLive reported in February that Jennifer Fairfield, owner of Garden Mill at 110 S. Main St., coordinated Wine, Women and Shopping and the Chocolate Extravaganza before she handed both events to the Chamber. Garden Mill closed early this year after 20 years downtown, according to MLive. So this is the first edition since the store that ran the event left Main Street.
The Chamber running it today is a different kind of chamber, too. In a September profile, The Sun Times News traced Sounds & Sights, winter curling, the chocolate and wine walks and late-night shopping back to the Chamber. Executive Director Terris Ahrens, who started on March 1, 2020, told the paper, "The fact is, the traditional chamber of commerce is kind of a dead industry." The Chamber hands out the bag and map, runs a market and the info booth, and leaves the specials to each store.
What a glass of wine costs depends on the door you walk through
Since nobody sets a single price, wine costs anywhere from free to $9 a glass within a few blocks. Here are the posted offers, which the Chamber says it updates weekly:
| Stop | Posted offer |
|---|---|
| Main Street Provisions | Free mulled wine and red wine washed cheese samples, both days |
| La Jolla | Free wine and chocolate truffles, plus 50% off sterling silver |
| Chelsea Home | Wine samples while shopping, plus a pop-up clothing boutique |
| Smokehouse 52 BBQ | $5 glass of red or white |
| Jet's Pizza | $5 house wine glass, $10 margs and mules |
| The Grateful Crow | $6 glass |
| JD's Stage Bistro | $8 glass, $15 flight of three 3-ounce pours |
| Common Grill | $9 featured red or white by the glass, both days |
| Merkel Furniture & Carpet One | Tasting flights with a ticket purchase |
Merkel is the only listing that mentions a ticket, and that ticket covers Merkel's own flights. The rest of the weekend has no entry fee. Some stops skip wine. Motley Crepe Co. is pouring free samples of a nonalcoholic Low Country Bourbon Sugar Black Tea, and Chelsea Farmers Supply has Chemex brewing demos with nonalcoholic spiced cider. Valiant Bar & Grill is taking 10% off the whole bill both days if you mention the event.
Friday is for the shops
Several of the best offers happen only Friday or run longer that day, so the store-by-store setup splits the weekend in two.
- Chelsea Painters holds a holiday art sale Friday only, 10 a.m. to 4 p.m., at Chelsea Depot, 125 Jackson St.
- V's Cards and Trading takes 10% off purchases of $20 or more, Friday only.
- Dragonfly Earth Essentials has tarot readings with Annora Brown from noon to 5 p.m. Friday. Saturday brings a different guest.
- Geek Brush Studio runs holiday Make & Take painting all day Friday at $15 per painting. Saturday's session ends at 2 p.m.
- FarmSudz stays open until 7 p.m. Friday and closes at 5 p.m. Saturday. It's debuting an event-only scent of its Handz lotion and People Polish scrub.
- Chelsea Village Flowers is open 9 a.m. to 5 p.m. Friday but only 9 a.m. to 1 p.m. Saturday, with holiday items marked down both days.
Friday evening, JD's Stage Bistro has free dinner music from The Jazz Circuit Riders from 5:30 to 7:30 p.m., no ticket needed. Put that after a 7 p.m. last stop at FarmSudz and you've used most of Friday.
Saturday stacks four markets into one window
Saturday adds markets on top of the store specials, and each one keeps its own hours:
- 10 a.m. The 15th annual Chelsea Depot Artisans Market opens with handcrafted goods from area artists and runs until 4 p.m. The Friends of the Chelsea District Library start their monthly used book sale, which ends at 1 p.m.
- 11 a.m. The Chamber's Visitor Center vendor market opens with the Kiwanis Club of Chelsea and Eclipse Yoga among its vendors, plus free Wine, Walk & Shop totes while they last. It runs until 4 p.m. Ugly Dog Distillery opens its 6th annual Markers Mart, a free sip-and-shop with chocolate martini specials and Cake by Kaity, until 3 p.m.
- Noon The Cheese Pull food truck parks at Ugly Dog until 5 p.m. JD's Stage Bistro opens early with free music from Ben Daniels until 2 p.m. and starts its "Check Under Your Glass" game, with stickers under four wine glasses for a $25 gift card or merchandise. WAVE rides begin and run until 6 p.m.
- 1 p.m. The book sale and Chelsea Village Flowers close.
- 3 p.m. The Markers Mart closes.
- 4 p.m. The Depot and Chamber markets close, and Geek Brush Studio opens a reception for the Michigan Watercolor Society's 79th Annual Exhibition that runs until 9 p.m.
All four markets are open together only between 11 a.m. and 1 p.m. If the book sale and all three vendor markets are on your list, that two-hour block is when to do them, and wine stops and lunch fit better later in the afternoon. The Watercolor Society reception is at Geek Brush Studio, 108 E. Middle St. The exhibition hangs from October 7 through November 21, so you can still see it after the weekend.
A stop with no posted hours is easy to miss. ART is for the BIRDS has a pop-up display out front of Susan Jacobs, CPA, at 102 E. Middle St.
Getting around, and where the evenings go
The Western Washtenaw Area Value Express, or WAVE, is listed as giving rides from noon to 6 p.m. during the event. No event stops or special fare have been posted. WAVE's general service listing gives most one-way fares as $0 to $5, booked by phone, email or the Ride Pingo app, so call ahead to check how event rides work. If you're driving, the City's DDA parking map, was last updated September 10, 2026.
The Purple Rose Theatre has performances both nights and Sunday the 8th. It's running Bastard, a world premiere by Devin Scillian directed by Rhiannon Ragland, through December 20. JD's free 5:30 to 7:30 p.m. jazz set runs again Saturday, so a Saturday could start at the Depot market at 10 a.m. and end with dinner music on South Main.
Downtown stays busy after the weekend. The Veterans Day Community Tribute starts at 8 a.m. on November 11 at Veterans Park, followed by a free breakfast at the Chelsea Senior Center. Breakfast reservations are due November 6, the opening day of Wine, Walk & Shop. Hometown Holiday follows with the tree lighting at Pierce Park on December 4 from 5 to 6:30 p.m. and the Light Parade down Main Street from Old US 12 to E. Middle Street at 6 p.m. on December 5. From December 1 through January 8, the Susan Jacobs windows switch from the bird pop-up to the Hometown Holiday gingerbread house display.
Weekends like this one tell you a lot about how a downtown runs, down to which shops stay open late and which corners fill up first. If you're thinking about a move within Chelsea or nearby and want to talk through what the town is like day to day, Charles by Reinhart would be glad to help. Schedule a Consultation, and we'll compare notes after the weekend.
