A shift in the Missouri River that deprived Weston of its riverboat port in the late 1800s could have signaled its death knell, but the small town survived and preserved its antebellum homes and parts of its Norman Rockwell–esque downtown. This charming community on the outskirts of Kansas City extends old-fashioned hospitality with its inviting boutiques, historic distillery, agricultural experiences, and many festivals.
What to do
Get your heart pumping at Weston Bend State Park, where miles of hiking and biking trails showcase the river, migrating birds, and native flowers. Learn about the region’s rich tobacco heritage from an interpretive display at one of the park’s 5 historic tobacco barns.
In keeping with its reputation for producing fine wine, spirits, and craft beer, Weston offers engaging tasting-room experiences. Holladay Distillery, which at one time was known as McCormick Distilling Company, has produced bourbon whiskey since 1856. Sign up for a 90-minute tour of the stillhouse just southeast of town ($25). At McCormick on Main downtown, enjoy craft cocktails along with 25-cent samples of the distillery’s branded spirits.
Located inside a former 1867 church, Pirtle Winery offers free tastings and sells award-winning wine, mead, and hard cider. Sip a glass on the deck or in the vine-covered wine garden. The Weston Brewing Company crafts an array of beers and is home to O’Malley’s 1842 Pub, an underground bar with a full schedule of live music. Brewery tours include the historic underground cellars ($5 for guests over 14).
Agritourism draws visitors to the area to observe working farms. At Weston Red Barn Farm, tour the barnyard and shop for produce from Memorial Day through Halloween. The site comes alive on fall weekends through November 11 with hayrides to the pumpkin patch (adults, $3.75) and more. Tours and tastings at Green Dirt Farm (starting at $17) show how sheep’s milk is turned into artisanal cheese.
Weston’s festivals provide plenty of reasons to visit. AppleFest on October 7–8 celebrates fall with a parade, autumnal food, vendors, and music. On October 28, the annual Weston Whiskey Festival pairs the malted grain spirit with cigars ($55 in advance).
Christmas celebrations start November 11 during the Weston Holiday Open House, when Father Christmas may appear at the tree-lighting ceremony. The magic continues on December 2 and 3 with the 40th annual Candlelight Homes Tour showcasing beautifully decorated residences and B&Bs ($20 in advance).
Where to shop
Where to eat
Located in a building that dates to 1842, Tin Kitchen serves Southern-style classics slow-smoked with pecan wood. Dig into Celtic menu favorites like the Stout Bangers and Mash and the Irish Egg Rolls made with corned beef at America Bowman Restaurant. The Meat Me in Weston is one of a dozen appetizing pies at The 640 Pizza and Pints.
Where to stay
At The Inn at Weston Landing, you’re greeted with pastries and old-world charm. All 4 of the inn’s rooms are decorated with antiques. Rooms are $200. The rooms at the Hatchery House Bed & Breakfast feature a refined rustic aesthetic. Enjoy the sunset from a second-floor deck if you reserve the Holladay Brothers Room. Rates start at $215.
Be sure to designate a driver if you plan to drink alcohol.
Travel offers & deals
Hot travel deals
Get the latest offers from AAA Travel’s preferred partners.
Travel with AAA
See how we can help you plan, book, and save on your next vacation.
Save big with AAA discounts on tickets to your next adventure.
Travel with confidence
Purchase travel insurance with Allianz Global Assistance.