Nearly every public event on Cottleville's October 2026 calendar takes place within a short walk of the corner of Fifth Street and St. Charles Street. Legacy Park, the city's park at 5490 5th St., is on one side. Frankie Martin's Garden, a private food-truck and drinks garden at 5372 St. Charles St., is on the other. Several events use both. A race starts on the park's paths and the party afterward happens in the Garden. The city's amphitheater page even sends concertgoers across the street to the Garden for food trucks.
Here is the month, taken from the City's October 2026 calendar and the Garden's own event listings.
| Date | Event | Where | Hours |
|---|---|---|---|
| Sat., Oct. 3 | Witches in Cottleville | Historic downtown venues, including the Garden | 3–11 p.m. |
| Sun., Oct. 4 | Barktoberfest 5K and 1-mile run/walk, then the festival | Legacy Park, then Frankie Martin's Garden | Races 9 and 10 a.m., Garden 11 a.m.–3 p.m. |
| Tue., Oct. 13 | Cottleville Arbor Day | Scott A. Lewis Park | 4–7 p.m. |
| Sat., Oct. 17 | Touch-A-Truck | Frankie Martin's Garden | Morning |
| Tue., Oct. 20 | Movie & Hayrides in the Park | Legacy Park | 6:30 p.m. start |
| Sat.–Sun., Oct. 24–25 | PRAC Family Camp Out and Star Gazing | Kochanski Multi Sports Field | 4 p.m. to 6 a.m. |
| Sun., Oct. 25 | Golf Cart Trunk-or-Treat | Frankie Martin's Garden | 2–5 p.m. |
| Sat., Oct. 31 | CWS Chamber Run Witch Run 5K | Legacy Park | 7 a.m.–noon |
Arbor Day at Scott A. Lewis Park is the only event in the table held outside the Fifth Street cluster. Kochanski Multi Sports Field may look like a different venue, but the City's amphitheater page puts it in the back of Legacy Park, where it serves as the park's rear parking lot. Sand volleyball leagues also play at Legacy Park almost every night of the month, from 6 to 11:30 p.m.
Why the Garden Works as the Park's Other Half
Frankie Martin's Garden was built on land with a local history. Frank J. Martin was a longtime Cottleville resident. He worked more than 50 years in maintenance at St. Joseph Church and School and was a member of the Knights of Columbus. According to the Garden's history, neighbors remember him as a regular at Bemo's and Jo's. His former house was restored and now serves as the Garden's centerpiece, known as The House, and the garden itself covers what was his property and farm.
The team that runs it also created 9 Mile Garden. Frankie Martin's Garden pairs rotating food trucks with more than 60 wines, a library of over 200 whiskeys and a lineup of Missouri breweries.
The two properties work together because each has what the other lacks. Legacy Park has open lawn, paved paths, an amphitheater and parking. The Garden has the food, drinks and permanent gathering space that a public park doesn't provide. The City's own amphitheater page reflects this. It suggests that concertgoers pick up dinner to go, mentions that food trucks are right across the street at the Garden, and links to a list of Cottleville restaurants.
October 4 Shows the Pattern Most Clearly
Yadi's Yummies is holding its 7th annual Barktoberfest this year. This year the day starts with chip-timed races in Legacy Park run by MSE Racing: a new 5K at 9 a.m. and a 1-mile run/walk at 10 a.m. Entry costs $35 for the 5K, $25 for the mile or $40 for both, and leashed dogs run free. At 11 a.m. the event moves across the street to Frankie Martin's Garden for vendors. All proceeds go to Annie's Fund, which helps pay for medical care for dogs and cats in rescues and shelters. The Garden's listing adds music, food trucks, raffles and a costume parade and contest.
The 5K is new this year, and the race listing puts Barktoberfest itself at Frankie Martin's Garden, with the morning's races in the park across the street. The month closes with another race in the park, the CWS Chamber Run Witch Run 5K in Legacy Park on October 31.
Golf Carts Connect the Two Sides
The amphitheater page shows how the City expects people to get to Legacy Park. It says the amphitheater "is designed for local visitors to walk, bike, or golf cart in." The first two aisles of the parking lot are reserved for golf carts, accessible parking and band loading. Golf carts are not allowed on the amphitheater hill or the grass.
The Garden plans around golf carts too. Its Halloween event on Sunday, October 25 is a Golf Cart Trunk-or-Treat from 2 to 5 p.m., with costumes encouraged. That same Sunday the PRAC Family Camp Out ends at Kochanski Multi Sports Field, so a family could take down a tent behind the park at 6 a.m. and be back in costume across the street that afternoon. The Twilight Tuesdays page said sign-up for the campout was "coming soon," so check with City Hall about registration.
Touch-A-Truck, from the Kolb Family Foundation, comes to the Garden on Saturday, October 17. Kids can get close to fire trucks, police cars, ambulances, SWAT vehicles, tractors and dump trucks. Admission is by donation, with a suggested minimum of $10, and all proceeds go to the Karen Weidinger Foundation.
What's Different in the Park This Fall
Vantage Lake is the quieter part of Legacy Park. The nine-acre lake has a 0.7-mile paved walking trail, a small gazebo, restrooms and a playground. You can reach it from Lohmar Lane by way of Madison Park Drive, or from the main park across a 10-foot-wide paved pedestrian bridge over Dardenne Creek. In his first State of the City address on June 17, 2026, the mayor said the shoreline stabilization project there was complete. The project addressed decades of severe erosion and included the beginning stages of restoring natural and native plantings meant to reduce future erosion, improve water quality and support a more diverse ecosystem around the lake.
If you want a longer walk after the Barktoberfest mile, plan around a closure to the east. Great Rivers Greenway's alert, posted August 24, 2026, says the Dardenne Greenway between Mexico Road and Dardenne Park is closed for construction of the new greenway, and the underpass beneath Mexico Road is closed for improvements. Both closures last through summer 2027. The alert names only that stretch. This section of greenway also passes the shelter and fishing dock at the east end of Harmony Lake in Legacy Park and the native-plant "botanical vignettes" along the St. Charles Community College campus.
Where to Eat Before or After
Food trucks at the Garden are the easiest option, but the Garden's food-truck events page currently reads "We are updating our events," so check its social channels the day you go.
These Old Town spots, all on the City's 2026 brochure map, are a short walk or cart ride from Fifth Street:
- Pink Willow Café & Rooftop, 5523 Oak St. Breakfast, coffee, lunch and weekend brunch, open Wednesday through Sunday from 8 a.m. to 3 p.m. Run Witch Run falls on a Saturday this year, so Pink Willow will already be serving when runners finish.
- Oak Street Inn & Lounge, 5521 Oak St. Owners Chelsey and Nick Sweeten spent several years building it out. The main restaurant focuses on steak, the rooftop serves flatbreads and salads, and the underground speakeasy has a modern Asian-fusion menu with sushi and poke bowls.
- Cottleville Wine Seller, 5314 Highway N. More than 200 wine labels, a large patio with heated seating and live music.
- Three Kings Pub, 5045 Highway N. This is the address where Salty's Fresh Mex closed in late 2024 after eight years. Three Kings opened its fourth location there, a 4,000-square-foot space with 125 indoor seats, and Ladue News's January 2026 restaurant roundup listed it among the new openings. Its menu is pub food: wings, burgers, flatbreads, pastas and seafood.
- Piazza Messina Winery & Venue, 5535 Highway N. Mostly an event venue on 14 acres. Its public "Sips" nights offer bistro food, brunch, happy hours and seasonal live music.
The Two Weeknights Worth Planning Around
Most of the month's events fall on weekends, but the calendar has two Tuesday events. Arbor Day at Scott A. Lewis Park on October 13 runs from 4 to 7 p.m. Movie & Hayrides in the Park on October 20 starts at 6:30 p.m. at the Cottleville-Weldon Spring Rotary Amphitheater. The City's calendar lists the movie night ending at 9 p.m. and the Twilight Tuesdays page says 8:30, so plan for a school-night bedtime either way.
On movie night, the City's directions apply. Bring blankets or chairs. Park on pavement at the park entrance next to City Hall or at Kochanski Multi Sports Field in the back, and keep cars off the grass. If you're coming by golf cart, use the reserved aisles near the front.
If you live close enough to Fifth Street to golf-cart to the hayrides and wonder how that location shows up in your home's value, Boutique Realty can give you a starting number. Get your instant home valuation, and we'll be happy to talk through what's behind it.
