With some great day trip options in the surrounding area, renting a car makes sense. Without one, it’d be much harder to experience all that Pittsfield, 25 miles away, has to offer. Explore the area starting with Old Orchard Country Club, John Greene Shastid House and Pike County Historic Museum. Don’t skip St. Louis either! Just 50 miles away, Forest Park, Fox Theater and Tower Grove Park are non-negotiable stops here.