Ask a Town and Country neighbor where the fall calendar actually happens and most will name a restaurant. Ask again and they will name a park. What they will not do is name five or six scattered spots, because there aren't five or six. There are two properties on Clayton Road, about a mile and a half apart, and between them they carry almost the entire season.
That is not a complaint about a lack of options. It is a fact about how this particular suburb organizes itself, and it changes how you plan a Saturday once the patio nights get shorter.
One Lake, Two Kitchens
Start at Blacksmith Grove, the barnwood-clad development at the corner of Clayton and Mason roads, built on seven acres behind the Straub's grocery store. The developer's original plans for the site called for an amphitheater, and the property backs onto a small on-site lake with a gazebo and walking paths. What actually got built on that lake is two restaurants that could not be more different, sharing the same water.
Wild Crush Wine Bar(n) opened first, the project of professional golfer Jay Delsing and interior designer Karen Paslawski, with their daughter Lexie running day-to-day hospitality. The concept is self-serve: guests load a card and pour their own two, four, or six ounce portions from a rotating list of a dozen reds and a dozen whites, priced by the ounce. The building runs about 1,800 square feet, small by design, with a patio that opens straight onto the lakeside park. Delsing has talked about the space hosting farmers markets, live music, and even a Christmas tree lot when the season turns.
A few doors down on the same property, Cleaver & Cocktail took the opposite approach. Marc and Amy Del Pietro and Brian and Lea Doherty, the team behind 58hundred in the city and The Block in Webster Groves, built a nearly 5,000 square foot steakhouse with a glass wall separating the dining room from an in-house dry-aging chamber. Their patio also faces the lake, and the same lakefront gazebo shows up in their own event planning for farmers markets and weddings.
So the choice most residents describe as "wine bar or steakhouse" is really a choice between two doors on the same lawn. That matters for planning a fall evening. If the patio at one is full, the other's is thirty steps away, facing the same water, with a genuinely different menu and price point. You are not driving across town for a backup plan. You are walking across a parking lot.
The Farm That Still Runs the Calendar
The second address predates both restaurants by two centuries. Longview Farm Park sits on what was once a 350-plus acre farm, acquired directly from the federal government in the 1820s. The current farmhouse started as a story-and-a-half log cabin built sometime in the 1870s, got wrapped in a white frame house by the 1920s, and passed through several private owners before the city bought the property in March 2000 and formally dedicated the park in September 2002.
What makes Longview the actual anchor of the fall and winter calendar isn't its acreage or its trails, though the trail is tree-lined, shaded, and genuinely popular with dog walkers. It's that the city runs three of its named recurring events here every year: the Turkey Trot, the Holiday Boutique, and an Art, Wine & Music event. None of those are generic parks-department filler. They are the specific programs the city's own parks staff builds a season around, and this year's Turkey Trot falls on Thanksgiving Day, November 26.
If you want the farmhouse itself for a holiday party, know that it books directly through the city's Facilities Supervisor rather than through an online calendar, and that the historic rooms and the newer gathering space can combine to hold up to 100 guests for a reception. That is useful information if you are already thinking about December, because the popular weekends tend to fill early.
Town Square Picks Up Where Longview Leaves Off
The third piece of this only shows up once summer's Friday night concerts wind down. According to the city's own August 2026 Board of Aldermen packet, the Winterfest team is already finalizing plans for a December 5 celebration at Town Square, and the board separately approved a contract with Fantasy Drone Shows to run a drone display at the city's 2026 Fire & Ice event. That is a new production element for a city event, not a repeat of last year's format, and it signals Town Square is being built up as the cold-weather counterpart to its warm-weather concert series.
Here is the shape of the season laid out together:
| Event | Location | Timing |
|---|---|---|
| Turkey Trot | Longview Farm Park | Thanksgiving Day |
| Holiday Boutique | Longview Farm Park | Fall/holiday season |
| Art, Wine & Music event | Longview Farm Park | Seasonal |
| Winterfest | Town Square | December 5 |
| Fire & Ice (with drone show) | Town Square | Winter 2026 |
Three of those five live at one park. Two live at one square. That is the whole public calendar, and it sits alongside the private one at Blacksmith Grove.
Three Addresses, Not Thirty
Search for things to do in Town and Country and you'll get pages of restaurant round-ups and attraction lists pulling in everything from a butterfly house to a transportation museum a few towns over. None of that is wrong, but it makes the city look sprawling in a way it isn't. The events the city itself invests staff time and drone contracts into, and the two restaurants that opened facing the same private lake, all sit within about a mile and a half of each other along Clayton Road.
That concentration is worth knowing for two practical reasons. First, it means the fall season here rewards showing up at the right property on the right week more than it rewards driving farther afield. Second, it explains why a weekend can start to feel repetitive if you're not tracking the specific dates. The Turkey Trot only happens once. The Holiday Boutique has its own window. Winterfest and Fire & Ice are new enough in their current form that missing them means waiting a full year for the next version.
A few practical notes for using the season well:
- Patio season at Blacksmith Grove runs until the first hard frost, so an October evening at either restaurant is a different experience than the same table in January.
- If you want the Longview Farm House for a private holiday gathering, call the Facilities Supervisor directly rather than searching for online booking, since dates fill by referral as much as by search.
- The Turkey Trot starts on Thanksgiving morning at Longview, so plan around it rather than assuming you can drop in after the fact.
- Fire & Ice's drone element is new for 2026, which means this year's version will likely look different from anything you remember from past winters at Town Square.
None of this requires a car full of gas money or a long drive toward Clayton or Chesterfield. It requires knowing that this particular fall runs through two properties and a handful of dates, not a scattered list of options.
If you're weighing whether Town and Country still fits your family's next chapter, or you're already here and thinking about what a move within the neighborhood might look like, Jeff Lottmann can walk you through what's actually happening street by street. Schedule a market consultation when you're ready to talk specifics.
