The 20th annual Walkin' on Main fills Old Town Cottonwood this Saturday, November 14, from 11 a.m. to 5 p.m. Admission is free. The festival has wine tasting, a classic car show, dog adoptions, local vendors and live music, according to the Verde Valley Wine Consortium's announcement. One ticket that day pays back into the street's buildings. It costs $5, it's sold at the Historic Preservation Commission's booth, and it pays for a docent-led walk through Old Town's history. The City of Cottonwood says the money goes to a grant program for the landmarked buildings the walk explains.
Saturday, Hour by Hour
The festival is sponsored by the City of Cottonwood and the Verde Valley Wine Consortium, and Paula Woolsey is the organizer. The festival's entertainment page has three bands across the day, and the history tours leave every 30 minutes from 11 a.m. to 2 p.m.
| Time | On Main Street |
|---|---|
| 11 a.m. | Festival opens; first Historic Property Tour departure; Toucan Eddy plays until 1 p.m. |
| 1:30 p.m. | Sweet Baby Rays Blue Smoke, until 3 p.m. |
| 2 p.m. | Last scheduled tour departure |
| 3:30 p.m. | Well Dressed Wolves close the music schedule at 5 p.m. |
| 7 p.m. | Acappella Sedona with regional guests at Old Town Center for the Arts |
The evening show is listed on Old Town Center for the Arts' fall program. It's a separate event from the festival, but it's on the same date and in the same district.
Nine wineries are pouring this year: Alcantara Vineyards, Arizona Stronghold Vineyards, Caduceus Cellars/Four Eight Winery, Da Vines Vineyard, Laramita Cellars, Oak Creek Vineyards, Omphalos, Page Springs Cellars and Southwest Wine Center. A six-tasting ticket costs $20 in advance and $25 on the day, and veterans get two extra tastings. Red Rock Collision presents the car show, and the festival site also lists art exhibits and retail vendors.
How the Tour Works
The Historic Preservation Commission runs the Cottonwood Historic Property Tour. It used to be called the Cottonwood Historic Home Tour, and its stops include homes, businesses and other properties. Participants follow a set route with docents who explain each stop. In its November 2 announcement, the City says the docents cover "the local history behind not only the properties but also many important figures throughout the years."
Tickets are $5 and sold only in person at the HPC booth during Walkin' on Main. The tour's own site says each departure has limited spots and suggests reserving a time slot at the booth early. If you want a midday tour, stop at the booth when you arrive and book it before you head to the tasting tables.
The tour isn't new. A 2021 Signals AZ article said it was returning after a two-year break. That year it ran virtually, with 14 properties, among them the Verde Valley Senior Center and Belfry Brewery. In 2025 it ran during the November 8 Walkin' on Main, with the same 30-minute departures and the same $5 price.
Where the $5 Goes
The City says the 2026 ticket money will fund its Historic Preservation Matching Grant Program, which is open to historic landmarked properties. The FY2027 grant packet, revised July 22, 2026, sets the terms:
- What it pays for: rehabilitation, preservation or restoration of a historic building's exterior, including roofs, windows and doors, walls, porches, signs, masonry, paint and historic details.
- Who qualifies: properties in the Old Town Special Planning Area, properties on the National Register, and designated local landmarks. Any other property has to be landmarked first.
- How much: up to $3,500 per project. The owner has to put up a cash match of at least 50% of the approved project cost.
- How it pays out: as a reimbursement, after the City inspects and approves the finished work.
Those are small amounts for a building owner. For a Main Street storefront they could cover a sign, a window repair or a coat of paint that matches the building's period, and those are the details the tour docents point out. These terms are general information from the City's published packet, not legal or financial advice. Owners thinking about applying should confirm eligibility and timing with the City and their own advisors.
The program has struggled to attract applicants. The City's 2023 Community Development annual report calls it a competitive 50/50 match for minor exterior improvements to landmarked structures and says "no applications for the matching grant were received for the 2023-2024 FY." The same report says the commission surveyed homes inside the Old Town Special Planning Area to see whether a residential historic district was feasible, and that it would keep applying each year for State Historic Preservation Office grants to move that work forward.
So the tour is one way the commission funds the grant, and it also introduces Old Town's buildings to the residents walking past them.
The Sponsors Are Main Street Businesses
The 2025 tour was sponsored by Taylor & Sons Hauling, Inc. and Wired-Up Systems, LLC. This year's sponsors are the Verde Valley Humane Society, Bananas in Old Town, Pawz On Main, Pizzeria Bocce Patio Bar and Spirit of Strength Boutique.
Spirit of Strength Boutique is one of the newest businesses on that list. The Verde Independent reported its opening at 1037 N. Main St., with owner Karla Nicol holding a ribbon-cutting on July 9, 2026. A shop that opened four months ago is now helping pay for the history of the street it opened on.
Two Weeks After the Flood
Walkin' on Main falls 13 days after the Verde River flooded the Bates Road area of Cottonwood on November 1, as the Verde Independent reported. On November 2 the City closed Riverfront Park entirely, citing flooding and unsafe conditions, with no reopening date set. On November 4, Mayor Ann Shaw issued a proclamation of emergency. The festival and tour were still on the calendar after both notices went up. Before you head out Saturday morning, check cottonwoodaz.gov and the festival site for the latest.
Yavapai County is also accepting flood debris for free at county transfer stations through November 30. The Verde Valley location is in Camp Verde, at 2600 E. Hwy. 260, according to the Verde Independent.
What's Next in Old Town, December 4 and 5
After the festival, Old Town's next busy weekend is in early December, and Saturday, December 5, packs three events into one day.
- Friday, December 4, 4 to 7 p.m.: the 15th annual VIP Wine & Chocolate Experience pairs wine and other drinks with chocolate at Old Town tasting rooms, bars and restaurants. Tickets are capped at 100 and picked up at Old Town Square, 1044 N. Main.
- Saturday, 11 a.m.: Cottonwood's 72nd annual Christmas Parade, with the theme "Christmas Traditions," leaves the Verde Valley Fairgrounds parking lot. It heads east on Cherry Street, turns left onto Main Street through Old Town and ends at N. Cactus Street, and the judges' stand is at Mingus and Main.
- Saturday, 3 to 7 p.m.: the 33rd Old Town Chocolate Walk runs through Old Town merchants, shops, tasting rooms and restaurants. Tickets and bags are picked up at the Civic Center, also known as the Cottonwood Community Club House, starting at 3 p.m. Tickets not collected by 6 p.m. may be resold, and refund requests close November 27.
- Saturday, 5:30 p.m.: the Old Town Tree Lighting, with Christmas music and carolers.
Old Town Center for the Arts has two more Saturday shows in November and December: Nathan McEuen on November 21 and Caravan Dreams on December 12, both at 7 p.m. On Sunday, December 20, Hydrangea Sky Movement Arts gives two Winter Solstice performances, at 2 and 7 p.m.
Some Verde Valley properties come with history attached: an Old Town address, a landmarked facade, a building the docents stop at. If you're thinking about what owning one involves, Katrin Themlitz is glad to talk it through over coffee on Main Street. Let's Connect.
