Cottleville is one of the most charming towns in St. Charles County if you’re looking for that historic small-town feel in the middle of a high-growth area.
Old Town is at the center of Cottleville, where everything happens. If you’re looking to spend a day in Old Town, we put together a guide on everything there is to do: where to eat, shop, stay the night, and what’s on the event calendar.
We help people move to Cottleville every month. Tell us what you’re looking for.
Thinking About Living Here?
Old Town Cottleville, MO
Walking down Route N, the main street through Old Town, you’ll find a unique blend of quaint shops, historic buildings, boutiques, and restaurants.
The historic district runs along Highway N from St. Charles Street down through Main Street, Oak Street, Chestnut Street and Fifth Street. Most of it is an easy walk from end to end.
There’s always something new going on. The City of Cottleville always has an event, pop-up, or new business coming to town. Many long-standing local businesses are here, but new events are always happening.
The city is also investing in the area. Announced in 2026:
- A new sidewalk on St. Charles Street connecting Old Town to the Timberwood Farms neighborhood
- On-street parking at St. Charles and 2nd Street
- Sidewalk, parking and drainage work on Lime Street and Chestnut Street between Highway N and Main Street
Things to do in Old Town Cottleville
Here’s what we’ll cover in this guide:
Local Food
Frankie Martin’s Garden
Frankie Martin’s Garden at 5372 St. Charles Street is the busiest hangout in Old Town Cottleville. It’s an outdoor spot that has:
- Local food trucks
- An indoor whiskey house
- Pickleball courts
- Sand volleyball
- Fire pits and pavilions
- A 26-foot LED screen for movie nights
There’s always something to do at Frankie Martin’s Garden, and they’re open 7 days a week.
The Garden is the outdoor space, with picnic tables, pergolas, and fire pits. On weekends, they host movie nights for everyone to hang out. The House is the indoor section: a historic house they converted into a hip whiskey-and-wine bar.
Park your golf cart in the dedicated lot behind the volleyball courts. More on that below.
Upshot Coffee
If you’re in Old Town Cottleville for the day, Upshot Coffee is where you’ll want to go for an amazing cup of coffee. The Cottleville shop at 5326 Highway N is the original, and Upshot now calls it the Upshot Coffee Flagship.
If you’d prefer tea or some fresh juice, they have that too!
They don’t just stop at drinks. Upshot also has fantastic sandwiches and pastries. Their cinnamon rolls are addictive and so are their croffles (croissant + waffle).
We made a video touring the whole town, and a lot of what’s on this page shows up in it:
22 minutes, 39 seconds
Living St. LouisPink Willow Café
Pink Willow Café is the chic little cafe attached to the Oak Street Inn & Lounge at 5523 Oak Street. It opened in the spring of 2024.
They serve breakfast bowls, coffee, brunch, and craft cocktails, making it a great spot to relax and enjoy a meal in the morning. Grab a table on the pink patio out front if the weather is nice.
Plank Road Pizza
If you’re looking for Cottleville’s best pizza, you’ll find it at Plank Road Pizza at 5212 Highway N. The name goes back to 1851, when the plank road brought the first settlers through the area.
Enjoy delicious, hand-tossed pizza made with fresh, local ingredients in the heart of Old Town. You’ve gotta try their chopped salad if you stop by!
Cookies and Cream
Cottleville Cookies and Cream, right next door at 5210 Highway N, is everyone’s go-to for ice cream and cookies in Cottleville. They’re always adding new flavors and post a new monthly special.
And if you can’t decide between cookies or ice cream, you can get both! Take any of their cookies and make it an ice cream cookie sandwich if you’re really hungry for dessert.
Bemo’s
Bemo’s at 5373 Highway N is a more traditional sit-down place to eat. It’s one of our favorite Cottleville restaurants, locally owned and operated, and a great spot for dinner or a date night in Old Town Cottleville.
Their menu really has everything from steaks, salmon, pastas, and even tacos.
Bemo’s seating options include the dining room, patio, bar, and banquet room. They also have live music from Thursday through Sunday every week!
Cottleville Wine Seller
At Cottleville Wine Seller, 5314 Highway N, you can sample local wines and enjoy a relaxing atmosphere. This local entertainment hub has over 200 labels of wine from around the world to choose from.
They’ve got outdoor seating, fire pits, and an upper-level deck where you can sit, chat, and taste great wine. They also have live music. Who doesn’t love that??
Mannino’s Market
Mannino’s Market is Cottleville’s favorite little market in the middle of town at 5205 Highway N. They’ve got the best steaks, deli, cheese, and pies in all of Cottleville.
Preparing a big meal? Bringing a dish to a friend’s? Looking for a pre-made meal to bring to work? Mannino’s has all of that.
Stop by and say hi on your way through Old Town!
Jo’s 5th Street Pub
Located in the basement of Mannino’s, you’ll find Jo’s 5th St Pub! This lively spot is where locals and visitors alike gather to kick back and have a blast.
We usually hang out at Jo’s after our annual Gateway client appreciation party across the street.
With its casual, inviting atmosphere, Jo’s 5th Street Pub is the perfect place to catch up with friends, cheer on your favorite sports team, or just unwind after a long day with a beer. They also added an open mic night in 2026.
And the best part? Their pub grub and wide selection of ice-cold drinks are sure to hit the spot every time. So, the next time you’re in Cottleville, make sure to swing by Jo’s 5th Street Pub, because you’re in for a fantastic time!
Local Shopping
Blooming Daisy Marketplace
The Blooming Daisy Marketplace at 5541 Chestnut Street is a local favorite shop in Cottleville.
You’ll find hand-crafted goods, vintage items, clothing, and home décor. The shop has a quaint boutique charm that reflects the atmosphere of Old Town Cottleville.
Lily and Day
A stop at Lily and Day is a must for all the fashionistas. This boutique was started in 2018 by 2 local moms who wanted to share their love of fashion with Cottleville.
In the summer of 2025, Lily and Day moved out of its old storefront and into Oh My Posh (A Gift Boutique) at 5247 Highway N, so you’ll now find it as a shop inside the gift boutique. Same clothing, accessories, home items, and personal gifts, one door down the street.
Their mission is to bring great quality products to women of all ages and styles who want something special to wear. Whether you’re shopping for yourself or getting a gift for someone you love, Lily and Day will have something unique.
The Craft Cottage
If you’re into arts and crafts, you’ll want to stop by The Craft Cottage at 5335 Highway N in Old Town Cottleville. They have a huge inventory of vinyl and glitter for any project you’re working on.
Plus, you’ll find all kinds of candy, goodies, and candles that smell incredible.
Where to Stay in Old Town: Oak Street Inn & Lounge
For a long time, Old Town had nowhere to spend the night. That changed in 2024 when the Oak Street Inn & Lounge opened at 5521 Oak Street, in the heart of the historic district.
The building has been here since 1862, when it opened as a general store. Over the years it operated as a post office, a hotel, and an antique store. Owners Chelsey and Nick Sweeten, who also own Public School House down the street, bought it in 2022 and spent about three and a half years rebuilding it.
They lifted the whole building and poured a new foundation underneath it, which is how a 160-year-old store ended up with a basement (and a speakeasy), and they added the Pink Willow Café onto the side.
It opened in phases: the Inn in May 2024, the Lounge that August, the rooftop soon after, and the speakeasy in March 2025.
Our team toured the building with Chelsey before it opened, and the video is still the best look inside:
12 minutes, 11 secondsLiving St. LouisThe Rooms
Oak Street Inn has 8 boutique rooms. Seven fill the second floor, and the third floor is a two-bedroom penthouse suite with a full kitchen that doubles as a getting-ready space for wedding parties.
Every room has its own theme, colors, furniture and finishes, so no two are the same. One of them opens onto the big second-floor balcony.
The Lounge and the Rooftop
Oak Street Lounge is the restaurant and cocktail bar on the first floor: upscale American food, a wraparound bar, booths, and a fireplace in the back.
The rooftop patio is on the third floor, with views out over Old Town. It’s a popular spot to watch a game outside.
The Root of the Oak Speakeasy
The basement they created by lifting the building is now The Root of the Oak, an underground speakeasy with an Asian-fusion menu (poke, sushi, gyoza) and a lineup of five different Old Fashioneds.
Here’s the fun part: the entrance is outside the building, down a set of stairs, and you need a code to get in.
They post a new code every day on their Facebook and Instagram stories.
So you can do a whole night on one block: coffee and brunch at Pink Willow, drinks on the rooftop, dinner in the Lounge, a nightcap in the speakeasy, and a bed upstairs.
Bross Brothers’ Cabin
Another fun place to stay is the Bross Brothers’ Cabin at 5366 Main Street. It’s a 200-year-old log cabin, original to the town, that’s been restored into a two-bedroom rental with a wraparound porch. You can walk to everything on this page from the front door.
Homes, neighborhoods, schools, parks and the golf-cart lifestyle, all in one guide.
Want the Full Picture of Living in Cottleville?
Read the Living GuideEvents & Wedding Venues
Public School House
Public School House at 5546 Chestnut Street is one of our all-time favorites in Cottleville.
From the Toasted Chestnut winter pop-up to the outdoor igloos they set up for the St. Patrick’s season, there’s always something fun happening. Tickets sell out fast, so act quickly if you want to buy a table during one of the pop-ups here.
We had our Gateway Realty Group Christmas party here and keep coming back.
Public School House offers individual tables during pop-ups for the public, and they also have wedding packages if you’d like to rent the whole place.
Piazza Messina
Piazza Messina at 5535 Highway N is one of Cottleville’s top wedding venues. It combines modern elegance with Italian country charm.
It features a beautiful indoor event space, an outdoor courtyard, and gorgeous views of the small lake. The lake is by far one of the best spots for wedding photos in Cottleville.
Its unique blend of style, flexible options, and exceptional service makes Piazza Messina one of the coolest wedding venues in St. Charles County. You don’t need a wedding invitation to get in, either: they host public brunches and evening “Sunset Sips” events through the year.
We even host our annual family photoshoots at Piazza Messina for all our past clients.
Le Champ de Fleurs by Stone Soup Cottage
If you’re looking for a smaller, more intimate setting, you’ll find it at Le Champ de Fleurs by Stone Soup Cottage, right down the street from Old Town at 5809 Highway N.
Stone Soup Cottage spent years as one of the region’s most sought-after French dinner reservations. After a pause, Nancy McConnell and her son Colin relaunched it in the fall of 2025 as Le Champ de Fleurs: the same spot and the same kitchen, now focused on small private events, ticketed wine-series dinners, and culinary travel rather than nightly service. The dinners sell out, so book ahead.
Its rustic charm and intimate setting make it perfect for couples looking for a cozy, romantic spot to tie the knot, and the top-notch service and high-end cuisine will have everyone talking about your day for years to come.
Outdoor Activities
Cottleville Caddy Shack
If you walk around Cottleville, you’ll see a bunch of golf carts!
Cottleville Caddy Shack on Lohmar Lane sells, services and rents golf carts and electric bikes, so you can get your own cart or rent one for the day to ride around Old Town. Whether you’re looking for a 1-person e-bike or a golf cart with room for 6, Cottleville Caddy Shack has you covered.
Golf Cart Rules in Cottleville
Before you drive one, know the city’s rules.
A cart needs a $25 permit from City Hall and an annual inspection, the driver has to be 16 or older with a license, and carts are only allowed on streets posted 30 mph or less. Lights are required after sunset.
In Old Town itself, carts stay on the roadways rather than the sidewalks, which are too narrow.
Look for the golf-cart-only spots along Highway N and the full lot next to the sand volleyball courts behind Frankie Martin’s Garden. At Twilight Tuesdays in Legacy Park, the first two parking aisles are reserved for carts.
If you’re going for a walk in Cottleville Trails, the neighborhood has golf cart parking around the lakes.
It is one of several neighborhoods in Cottleville worth walking before you buy here.
Legacy Park
Craving some outdoor fun? Visit Legacy Park on Fifth Street, which offers walking trails, two playgrounds, the Rotary Amphitheater, sand volleyball, basketball and tennis courts, a dog park, a community garden, two fishing lakes, and picnic pavilions.
It’s the perfect spot for a picnic or a social get-together, and the log cabin at the back of the park is the trailhead for the Dardenne Greenway, a paved trail along Dardenne Creek that you can walk, bike, or golf cart.
If you’re a golfer, Old Hickory Golf Club is right down the street from Old Town Cottleville. It’s a private club, so you’ll need a member to get you on the course.
For a touch of history, visit St. Joseph’s Church and Cottleville Cemetery. Dating back to the 1800s, this historic site provides a fascinating glimpse into the town’s past. While you’re at it, visit the Cottleville Veterans Memorial to pay tribute to the brave individuals who have served our country.
Local Events
Of course, one of the best things about visiting historic Cottleville is getting involved in local events. Here’s what’s on the calendar in a typical year:
- March: the Shamrock Run 5K from Fire Station #1 in the morning, then Cottleville Irish Fest through the afternoon and evening, spread across Public School House, Oak Street Inn, Piazza Messina, Frankie Martin’s Garden and the pubs. Both were on March 14 in 2026.
- May: Cheers Charity Fest, a pub crawl where your shirt is your ticket and the money goes to the charity you pick. May 9 in 2026, 14 venues.
- Summer: Twilight Tuesdays, free concerts at the Rotary Amphitheater in Legacy Park, 6pm to 8:30pm.
- October: Witches in Cottleville, the Chamber’s adults-only downtown party with 75+ vendors. October 3 in 2026.
- December: the Salvation Army tree lighting at the clock tower, and the winter pop-ups at Public School House.
Check out the town’s event calendar to see what’s happening during your visit. There’s always something fun going on if you’re looking for fun trip ideas.
So there you have it! Old Town Cottleville is a charming historic district that packs a lot into a few blocks. Whether you’re a history buff, a foodie, or just looking for a charming escape, this town has you covered.
Pack your bags and get ready to make some unforgettable memories in Cottleville’s adorable downtown area.
If you’d like to stay longer than a visit, you might really enjoy living in Cottleville. It’s one of the fastest-growing towns in St. Charles County, and many people have made the move here.
Moving to Cottleville, Missouri
Cottleville is a fantastic town to visit. But you know what’s even better than visiting? Living here!
If you’re in the market to move to Cottleville, please get in touch! We’re a well-known real estate group in the area, and we’ve helped countless clients strategize their move here.
Sharing our knowledge of local towns like Cottleville is our favorite part of working in real estate, and we’d love to help you.
We’re Excited to Work With You!
Someone from our team will reach out within one business day.