- Our list of the best things to do in Chesterfield, Missouri, features the top 227 nearby activities — including 82 great attractions with user approval ratings of 90% or more!
- Chesterfield, MO has a variety of great sights and experiences nearby. Top categories include: Outdoor Places, Amusement, Entertainment & Shows, and Sports & Fitness.
- The results below include the top 18 things to do within the city of Chesterfield, MO , followed by 209 popular activities in nearby cities, including St. Louis, St. Charles, Florissant, Ballwin, St. Peters, Maryland Heights, Fenton, Grafton, Eureka, Augusta, Arnold, O'fallon, Wentzville, Granite City, Defiance, Hazelwood, Boonville, Jefferson City, Kirkwood, Maplewood, Wildwood and Wright City
Showing 301-310 of
316
37.7 Miles
Open seasonally, The Weingarten is a family owned and operated winery and wine bar modeled on the area's historic German farms. The winery has scenic and expansive grounds, and hosts weddings and other events.
37.8 Miles
A family run horse facility, Liberty Prairie Farms provides quality care for horses. Also for horse enthusiasts, the farm offers both horseback riding lessons and training in horse handling. Other services include saddle fitting, boarding and horse leasing.
39.6 Miles
88%
42 votes
3718 Grant School Rd, New Haven, MO 63068
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The Bommarito Estate Almond Tree Winery owns a small vineyard, a wine tasting room, and an area where visitors can have a picnic by bringing their own food. The winery also hosts special events.
39.9 Miles
Open since 2003, Bo's Hollow replicates rural life in the 1930s. Guests can wander through the hollow and see sights like an outhouse and a working windmill, and then take a 15 minute ride in a Model A.
43.9 Miles
Part of the 20 miles-long Hermann Wine Trail, the Oak Glenn Vineyard & Winery offers its visitors a selection of 17 wine specialties. Besides the special events it organizes around the year, it can also host private events, such as weddings.
46.2 Miles
Hermannhof Winery & Sausage Shop is a historic winery that is listed on the National Register of Historic Places. The winery won the Brown-Foreman Trophy for 'Best New World White Wine'.
46.2 Miles
33%
3 votes
338 E First Street, Hermann, MO 65041
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The Three California Vineyards Tasting Room in Hermann offers tastings of wines from three distinctive vineyards: Dierberg, Star Lane, and Three Saints. All of the vineyards have won a variety of awards for their wines.
46.3 Miles
A winery with an inn on the premises, the Hermannhof Winery makes and bottles a variety of wines. The winery welcomes visitors, and holds regular tastings with food pairings in the tasting room.
46.4 Miles
Located in a small, historic building, the non-profit Show Boat Community Theatre hosts an array of performances. It presents dramatic and musical productions by the local community theater group, and hosts touring performers, as well.
46.5 Miles
The Hermann Wine Trail is a 20 miles-long river trail, which connects 7 family owned wineries between Hermann and New Haven.