Updated October 2026
Disclosure: This post may contain affiliate links, so I earn a commission if you decide to purchase through my links, at no cost to you. The Heritage House hosted our stay. All photos and opinions are mine.
Let me introduce you to one of my favorite towns – Weston, Missouri. This town of less than 2,000 people, located northwest of Kansas City and about 20 minutes from Leavenworth, Kansas, has been voted the #1 Best Day Trip by Ingram’s Magazine.
I adore Weston for its abundance of shops and attractions, including wineries, distilleries, and unique lodging, which is why we’ve visited more than once.
In 1929, Weston was the largest town in Platte County. On any given weekend, particularly during the fall season, Weston is bustling with activity downtown and beyond at its renowned distillery, wineries, orchards, and pumpkin-producing farms.
If you like to explore outdoors, the area provides stunning trails and an overlook you don’t want to miss at Weston Bend State Park. Bringing a dog on your trip? You’ll feel welcome at the Weston Dog Park.
Weston, Missouri: Making the Most of a Weekend Visit
During a fall weekend, I spent as much time as I could in Weston soaking up sunny days, strolling Main Street, and shopping unique boutiques.
From home decor stores with shelves lined with candles and specialty food items to one-of-a-kind shops stocked with artwork or antiques, Weston has it all.
The town was established in Northwest Missouri in 1837 and sits near Weston Bend State Park, a must-stop for those who prefer to opt outside and enjoy tree-covered trails for walking or biking, overnight camping areas, or an off-leash dog park.
SIP & SAVOR
O’Malley’s 1842 Pub
On our last visit to Weston, we skipped the brewery because we were short on time and the annual Irish Fest was underway – the area was crawling with tourists! I wasn’t going to miss experiencing the brewery and restaurant this time around.
Although we didn’t reserve a tour, which is recommended, we convinced an employee to give us a short walk-through tour of the O’Mally’s 1842 Pub.
Founded by German immigrants, Weston Brewing Company has operated since 1842. The walls are covered in black-and-white photos from the past.
The cellar pub was originally used to make lager beer and was built six stories underground. It closed during Prohibition and remains the second oldest brewery west of the Hudson River.
Sitting there, sipping a Guinness and admiring the stone walls covered in historic memorabilia, we felt transported to 1842, when the original brewery opened.
PRO TIP: Ask an employee about the “stairs under the stairs.”
American Bowman Restaurant
After enjoying our refreshing craft beers at O’Malley’s 1842 Pub, we headed back upstairs to the American Bowman Restaurant for a bite to eat for lunch.
I was a bit disappointed to learn the restaurant was out of Hand-Rolled Soft Pretzels, but we thoroughly enjoyed the Sausage Sampler and Irish Eggrolls.
The restaurant menu looks like a newspaper and includes a list of upcoming events and the building’s history.
Tin Kitchen
Noted for some of the best ribs in the Kansas City area, the Tin Kitchen stays busy serving authentic barbecue meats and yummy side dishes.
We were able to snag a two-top table within 10 minutes of waiting at the hostess desk, which was surprising since it was in the middle of their Saturday lunch rush.
Expect a short wait if arriving at the Tin Kitchen for lunch or dinner on a busy weekend.
We dined on barbecue ribs (of course!) and opted for the homemade mac-n-cheese and baked beans for our mouth-watering side dishes. The slow-smoked meat is prepared for up to 16 hours over pecan wood.
We loved the service. The waitress requested that the kitchen staff split our lunch order without us having to ask for it.
Pirtle Winery
Perhaps you’ve sipped wine in church before, but not like this! Established in 1978, the family-owned Pirtle Winery opened inside Lutheran Evangelical Church built by German immigrants in 1867.
The winery has been family-owned and operated since 1978.
We enjoyed a wine flight in the tasting room, located on the top floor as you enter the outdoor stairs. I was impressed by the award-winning wine selection.
I went outside my comfort zone and selected their famous Blueberry Mead as one of my flight selections. Noted to be “a blend of orange blossom honey and fresh blackberries,” I was impressed by how much I enjoyed its flavor. The selection has earned the family multiple gold medals and came highly recommended by a local store owner.
One of the white wines I sampled was poured from a can. They sell wine by the bottle, but three of the varieties come in 4-packs. You can also purchase wine by the bottle.
The winery opened The Vineyards at Pirtle Winery, a pizza and paninis cocktail and wine bar in walking distance of the winery’s tasting room. It’s open on Fridays and Saturdays.
The 640 Pizza and Pints
On a busy Saturday afternoon, we visited The 640 Pizza and Pints, but unfortunately the wait for a table was 45 minutes to an hour. So. we ordered a 16″ speciality pizza to go and took it to Weston City Park for a picnic seated at a gazebo table.
The supreme-style pizza was delicious, and the natural setting adjacent to Bear Creek made the experience spontaneous and fun.
Weston Wine Company
If chatting with friends or family over a bottle of wine seated on a patio sounds like the ideal afternoon, you’ll appreciate Weston Wine Company.
Known for build-your-own wine flights, the tasting room’s wine selection is sourced from across the globe.
Sitting on the front porch, we enjoyed a bird’s-eye view of downtown activity. Weston Wine Company’s game collection will impress you if you like to play trivia or board games while imbibing.
Green Dirt Farm Creamery
Look for the pink picnic tables and the stone building, and you know you’ve arrived at Green Dirt Farm Creamery.
Known for producing handmade artisan cheese and soft-serve ice cream with 100% sheep’s milk, the creamery is a popular place to shop and dine.
The ice cream is creamier than typical soft-serve and tastes richer in flavor, similar to a custard. We had already eaten lunch, so we skipped ordering a cheese sandwich, opting instead to buy a wedge of cheese to savor with wine at our vacation rental.
PRO TIP: Parking is limited. You may need to find a spot in the lot on the opposite side of the building.
The Cellar at Cactus Creek
You might miss The Cellar at Cactus Creek if you didn’t hear about it from a local. The basement lounge, located underneath a boutique clothing store, is a self-serve bar.
Simply select the canned beer or non-alcoholic beverage of your choice and pay for it upstairs when you’re done.
We loved the concept so much that we returned for a second visit, and this time we joined others downstairs, where people watched a televised football game or played board games.
PRO TIP: Look closely at the table lamps and furnishings. Some items are for sale.
The Upper Snug at Celtic Ranch
Another tucked-away bar and lounge at The Upper Snug within The Celtic Ranch. The hidden tasting lounge specializes in serving Irish whiskey cocktails, malt scotches, American bourbon, and craft beer.
To access The Upper Snug, walk inside The Celtic Ranch through The Whiskey Snug and take the spiral staircase to the second floor.
It’s a members-only space from Monday through Thursday, but opens to the public for tastings and pours on Fridays and Saturdays.
Don’t leave without shopping downstairs at The Whiskey Snug and for imported Irish clothing and souvenirs at The Celtic Ranch.
Other places to dine downtown include Avalon Cafe, The Royal Deluxe, Blue Jay Nutrition, and Weston Coffee Roastery.
SHOPPING DOWNTOWN
One of the best reasons to visit Weston is for the quaint shops. Main Street is lined with independently owned businesses, ranging from antique shops to home decor stores.
It’s best to shop downtown Wednesday through Saturday to access a majority of the stores.
The following stores are some of my favorites along Main Street.
Buffalo Ranch Home Furnishings
Buffalo Ranch Home Furnishings is stocked to the brim with home accents, candles, jewelry, seasonal decorations, and a bunch of other cool stuff you don’t need but totally want.
1837 Emporium
Inside the 1837 Emporium, you’ll discover antiques, collectibles, handcrafted items, and fine art. If you’re looking for a unique relic to display at home or to purchase for someone, this is the place.
I heard one woman exclaim how much she loved the store’s “pretty stained glass.” The store’s motto fits. It’s a place with “an eclectic faire.”
Renditions Polish Pottery Shop
Step into Rendeitions Polish Pottery Shop to peruse tables and shelves brimming with hand-painted dishware. An exclusive Midwest agent for Manufaktura Polish Pottery, each imported piece is uniquely designed and often showcases intricate patterns and a trademark blue color.
If you know someone of Polish heritage, they’ll likely appreciate any gift from the store.
PRO TIP: Don’t miss bonus pottery inventory on display in the basement.
La Bella Cucina Italian Market
One of the most notable stores downtown is La Bella Cucina Italian Market because it’s rare to find a shop in Kansas selling exclusively Italian imported gourmet food products. From top-quality olive oil to dried pasta, the store makes short work of deciding what to make for dinner.
PRO TIP: Sample wine in the rear of the store before purchasing a bottle.
Beverlin’s Statuary
Not only is Beverlin’s Statuary a great place to shop for cast-stone outdoor garden decor, but the towering Bigfoot sculpture at the entrance makes for a photo-worthy capture.
Northland Artist’s Gallery
Step inside Northland Artist’s Gallery to appreciate a variety of media, from oil paintings to handcrafted jewelry.
We chatted with the owner, who introduced us to the gallery’s furry feline. The laid-back vibe is welcoming, and you’ll be glad you stopped to view the work of Midwest artists, which is available for purchase.
Downtown Weston is home to various specialty stores and boutiques. You can find a complete list here.
TAKE A TOUR
Weston Historical Museum
Uncover the history of the town at Weston Historical Museum, a free-to-tour collection of artifacts and stories dating back to the founding of the Missouri River port town.
A self-guided tour of the museum took us about thirty minutes, but someone who wants to take a deep dive into the town’s bygone days could easily spend about an hour.
Don’t miss the five-panel timeline outside that starts with the town’s establishment in 1837, noting tobacco farming and distilling milestone years, and ending with the town’s 175th anniversary in 2012.
Weston Orchard & Vineyard
Weston Orchard & Vineyard, open May through November, is a must-visit you-pick farm.
During our late October visit, much of the apple orchard was pretty well picked over except for fruit on the tallest branches, but it was still an entertaining experience given how much there is to do on the farm.
Families love The Play Zone, petting zoo, ziplines, and two-acre corn maze. Other fall-only activities include Hay Mountain, Corn Crib, and an old-fashioned carousel.
We kept our visit low-key, choosing to shoot fall-themed photos from the “big chair,” and ate cider donuts while sipping a flight of hard fruit ciders. A band played live music on the patio.
Inside, the tasting room also sells wine by the glass. Stock up on jarred apple butter, salsa, or pies before departing for home.
Holladay Distillery
Known for its rich history of producing bourbon, Holladay Distillery was established in 1856 by Ben Holladay, who originally acquired the Pony Express.
It is operated by the McCormick Distilling Company (you’ve heard of the vodka, right?) and is the total experience for booze-loving tourists.
The grounds at Holladay Distillery are expansive and stretch as far as your eye can see from the road. An outdoor patio and Adirondack chairs on the lawn are preferred gathering places.
In the early 1800s, Ben Holladay purchased gallons of whiskey for 25 cents and then sold a sample shot for the same price.
Today, the distillery is well-known for its tasting room. You can also enjoy the same experience in the Holladay on Main tasting room and retail experience downtown.
You’ll pay a small fee for tastings, and a seasonal cocktail like the one pictured above costs around $15.
AMAZING ACCOMMODATIONS
The Heritage House
When you’re seeking a tranquil getaway surrounded by countryside and sunset skies, nowhere is better for an overnight stay than The Heritage House. Located a ten-minute drive from Weston, the restored farmhouse was the secluded retreat we needed to restore ourselves.
The farmland’s original owner saved the 1900s structure and slowly brought it back to life, adding wall-to-wall windows. His handiwork is also evident in the reclaimed wood and vaulted ceilings.
The current owners have upgraded this two-bedroom, two-and-a-half-bathroom home with modern luxuries and a country aesthetic. It’s the ideal, romantic getaway for a couple because the lack of distractions and patio conversations help you reset.
Memory foam mattresses are extra soft for those who want to feel enveloped while they slumber. You’ll feel spoiled, stepping out from the deep soaker tub to radiant heated bathroom floors.
Hilton2 Suites by Hilton Leavenworth Downtown
Over the years, we’ve also stayed at the spacious Hilton2 Suites by Hilton Leavenworth Downtown, where we enjoyed generous amenities including a complimentary breakfast, and our dog was welcomed.
OTHER NEARBY TOWNS
Make a point to visit the nearby town of Leavenworth, Kansas, just over the bridge and across the state line, or consider exploring the Historic Charm of Atchison, Kansas, the home of aviation pioneer Amelia Earhart.
