Special Report

40 Charming Small Towns to Visit This Fall

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11. Oakland, Maryland

Known as the “great small town,” Oakland is located amid the mountains of southern Garrett County. The town offers visitors shopping, restaurants, and historical sites, including a 19th-century railroad station. It’s also home to a recently created arts and entertainment district, hosting many arts-related events. In the fall, the area holds its annual Autumn Glory Festival, celebrating the local foliage with parades, concerts, exhibits, antique and craft shows, and more. Visitors can additionally venture just nine miles north to Swallow Falls State Park to experience the area’s natural beauty and the largest waterfall in the state.

12. Petersham, Massachusetts

Founded in 1754, Petersham is located among the forests of central Massachusetts. The town is home to history and natural beauty, including its Town Common and thousands of acres of conservation land. Outdoor lovers have plenty of opportunities to hike, bike, canoe, kayak, fish, bird watch, and more. Visitors can also check out the Fisher Museum, with dioramas that illustrate the history of woodlands that have been used by Harvard University for its forestry program for over 100 years. Nearby, visitors can explore the remnants of what used to be the town of Dana, or the ruins of an old prison complex in Rutland State Park.

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13. Munising, Michigan

Munising, located in the Upper Peninsula of Michigan, along the shores of Lake Superior, offers national parks, 15 waterfalls, five lighthouses, and more outdoor attractions. Highlights include the Pictured Rocks National Lakeshore, with its sandstone cliffs along the lake. There is also the Grand Island National Recreational Area, which visitors can tour by foot, bike, or bus. The Hiawatha National Forest offers 800,000 acres of woodland, and is home to 280 lakes and over 77 miles of Great Lakes shoreline.

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14. Lilydale, Minnesota

Promising the “feel of country and city,” Lilydale features parks and trails, perfect for outdoor enthusiasts, as well as a lively business community with shops and restaurants for a more urban experience. The 636-acre Lilydale Regional Park — like the town — gets its name from its abundance of lily pads. The Big Rivers Regional Trail connects this park with Ft. Snelling Regional State Park, home to the Historic Fort Snelling, built in 1825. The park is known for its bird- and other wildlife-watching.

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15. Parkville, Missouri

This historic town, settled in 1838, is located on the banks of the Missouri River, not far from Kansas City. Downtown Parkville features a mix of architecture dating from the mid-1800s to today. Visitors can enjoy shopping and dining, along with browsing for antiques and checking out contemporary art galleries. The area also features two nature sanctuaries — Sullivan Nature Sanctuary and Parkville Nature Sanctuary — that include 115 acres and about three miles of hiking trails.