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Weston, Missouri: Making the Most of a Weekend Visit

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Let me introduce you to one of my favorite towns — Weston, Missouri! This charming town, located northwest of Kansas City and only 20 minutes from Leavenworth, Kansas, has been voted The #1 Best Day Trip by Ingram’s Magazine 15 years running. I love Weston for its abundance of shops and attractions including a brewery, winery, and seasonal entertainment!

During a fall weekend, I spent as much time as I could in Weston soaking up sunny days strolling Main Street 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 antique cameras, Weston has it all!

The town was established in Northwest Missouri in 1837 and sits nearby Weston 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.
The shops are the main attraction in Weston’s historic district. People travel to the area to visit the locally-owned boutiques and artists’ spaces. It’s not uncommon to walk into a shop and find an artist at work on their craft. View the town’s store directory here.

Weston Brewery Company

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 not necessary but recommended, we did convince a very nice employee to give us a short walk-thru tour of the O’Mally’s 1842 Pub. (Brewery tours are available at 1 pm, 3 pm & 5 pm on Saturdays. Expect a one-hour tour of the brewery, underground cellars, the secret 4th cellar, and tasting. Tickets are $5 for anyone over 14, and younger visitors are free.)

Established by German immigrants, Weston Brewing Company has been operating since 1842. The walls are covered in black and white photos of the past. It’s tough not to be in awe of the operation’s historical roots.
Can you see me? This is the hallway that leads into O’Mally’s 1842 Pub, an underground space where they host Celtic bands. You must experience it!

If you love visiting museums and enjoying a craft beer or cocktail, you’ll definitely appreciate visiting the underground pub. Just sitting there while gazing at the stone walls covered in historic memorabilia, I felt like I had transported by to 1842 when the brewery was established.

The cellar pub originally used to make lager beer and was built six stories underground. It was closed during Prohibition and remains the second oldest brewery west of the Hudson River.

American Bowman Restaurant

After enjoying our refreshing craft beers, we headed back upstairs to the American Bowman Restaurant for a bite to eat for lunch. Although I was a bit disappointed to learn the restaurant was out of Hand-Rolled Soft Pretzels (they must have been hoarding them for the Irish Fest the next day?), we thoroughly enjoyed the Sausage Sampler and Irish Eggrolls.

This is the restaurant menu, which looks like a newspaper, and includes a listing of upcoming events and the history of the building.

Tin Kitchen

Noted for some of the best ribs in the Kansas City areas, the Tin Kitchen stays busy from 11 am-9 pm 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 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. Their meat is slow-smoked for up to 16 hours over pecan-wood. When making the most of a weekend in Weston’s historic district, make sure to leave time for a stop at Tin Kitchen.

We loved the service at Tin Kitchen. The waitress had the kitchen split our lunch order without even having to ask her.

Pirtle Winery

Perhaps you’ve sipped wine in church before, but not like this! Established in 1978, the family-owned Pirtle Winery is inside a former Lutheran Evangelical Church that was built by German immigrants in 1867.

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 selection of wines. 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 at $24.95 each.)

I found the stained glass windows inside the Pirtle Winery’s tasting room to be beautiful!

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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 with how much I enjoyed its flavor. The selection has earned the family multiple gold medals and came highly recommended by a local store owner. When in Weston, make sure to stop at the winery!

The Pirtle Winery has been family-owned and operated since 1978.

Shopping

The best reason to visit Weston, Missouri is for the town’s quaint shops. Main Street is lined with independently owned businesses ranging from an antique camera store (the man who works there is the sweetest and he is incredibly knowledgable!) to multiple home interior decorating boutiques. During our recent visit, I made sure to return to Buffalo Ranch Home Furnishings, a store stocked to the brim with holiday decor, home accents, candles, jewelry, and a bunch of other cool stuff you don’t need but totally want!

Shopping for gifts and collectibles is easy in Weston! Every store is anchored by a friendly shop employee and the shelves are lined with cute items from coffee mugs to aromatic soaps!
If you don’t find an open, free parking spot on Main Street, there are a couple of lots available in the historic district or you can park on adjacent streets.

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. Today, 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. Look at that cute pup! Sasha enjoyed relaxing with us outdoors after our tasting room experience.

My only regret is that we didn’t think ahead to reserve our spots on the afternoon tour of the distillery, but that’s another great reason to return to Weston! The highly-rated tour experience costs $10 for adults and allows you to “see, smell, taste, and touch real Missouri bourbon being made using the original recipe from 160 years ago.”

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 25 cent shots in the tasting room. You can also enjoy the same experience in the “McCormick on Main” tasting room in town.

If you’re looking for a fun weekend of dining, drinking, and shopping in a town with friendly locals and small-town charm, add Weston to your road trip itinerary. There is more than enough to do to fill the weekend if you take advantage of all of the area’s entertainment options. If you need lodging, Weston has cute bed and breakfasts. We stayed at the spacious Hilton 2 Suites in Leavenworth where we enjoyed generous amenities and our dog was welcomed.

There is always something going on in Weston! View upcoming events. If you’re in the area, also make a point to visit the nearby town of Leavenworth, Kansas just over the bridge and across the state line. Love the historic aspect of a small town? Consider adding Abilene, Kansas, the boyhood home of U.S. President Dwight D. Eisenhower.

Thinking of visiting Weston, Missouri? Pin the image below to our Pinterest board!