Charlottesville Fall Fun Bucket List

Written by Jess McCurry - September 13, 2024

Top Charlottesville Fall Activities

1. Explore Shenandoah National Park

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No fall bucket list in Virginia is complete without a visit to Shenandoah National Park! Best Hiking Trails for Fall Views:

Old Rag Mountain: A challenging 9.4-mile hike with panoramic views of the fall foliage.
Stony Man Trail: A shorter, family-friendly 1.6-mile round-trip trail offering stunning autumn vistas.
Hawksbill Mountain: The highest peak in Shenandoah, providing 360-degree panoramic views of the valley below. Moderate difficulty 1.7-mile round trip hike.

2. Pumpkin & Apple Picking

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Chiles Peach Orchard & Farm Market

Famous for its peaches in summer, Chiles Peach Orchard is filled with fall colors in September and October, and features one of the best pumpkin patches in the Charlottesville area. Located in Crozet, this farm also offers Virginia apple picking, hayrides, and delicious seasonal products like hot apple cider and fresh apple pies. The annual Pumpkin Festival is a can’t-miss event, filled with games, food, and family fun activities that celebrate the fall season.

Carter Mountain Orchard

As you drive up the winding road to the top of the mountain to find your perfect pumpkin you'll be greeted by views of the Blue Ridge Mountains views and apple orchards. In the fall apple picking is available for varieties like Fuji, Granny Smith, and Pink Lady. After wandering through the orchard and picking your apples relax on the deck to live music with local cider and wine. The market also sells additional local produce, homemade apple cider, and their famous apple cider donuts!

Middle River Farm

This family-operated working farm offers everything from traditional orange pumpkins to unique heirloom varieties. They are the Charlottesville home of the “wagon deal”, pick your own pumpkins and fit everything you can into one of their wagons for $40!

Henly's Orchard

Henly's in Crozet has a less busy and family-run atmosphere compared to larger orchards like Carter Mountain. Enjoy tractor rides, pony rides, petting zoo, and apple picking with friends and family.

Corner Store Garden Center

This country store in Ruckersville is a local favorite for those seeking a rustic and authentic pumpkin-picking experience. In addition to offering a pumpkin patch, this charming farm store features fresh produce, fall-themed products, and homemade goods. It’s a great spot to pick up seasonal treats and enjoy the beauty of fall in a more traditional, small-town setting. Don’t miss their Fall Festival on September 28, 2024!

3. Visit Downtown Charlottesville

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Downtown Charlottesville comes alive in the fall with seasonal events offered alongside the local shops and restaurants. Don’t miss these fun Halloween events downtown:

Doggie Howl-O-Ween: doggie trick-or-treating at local businesses on the Downtown Mall, and a costume contest!
UVA's Trick-or-Treating on the Lawn: every fall families flock to the UVA lawn for this annual event, students pass out candy from the historic pavilions.

4. Attend a UVA Football Game

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Fall in Charlottesville wouldn’t be complete without experiencing the excitement of a UVA football game. As the crisp autumn air settles in, game day at the University of Virginia becomes an unforgettable experience. The vibrant fall foliage on campus and the electric atmosphere of fans cheering for the Cavaliers make it a must for any fall bucket list.

5. Go to a Corn Maze

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Blue Ridge Mountain Maze

Liberty Mills Maze

Home to Virginia’s largest corn maze, but it’s also a great spot for pumpkin picking. Located in Somerset, the farm offers a wide variety of pumpkins in different shapes and sizes, perfect for carving or decorating. In addition to the pumpkins, Liberty Mills hosts fun fall activities such as hayrides, corn mazes, and opportunities to purchase fresh, locally-grown produce. A visit here guarantees a full day of autumn fun for all ages.

Blue Ridge Mountain Maze

This year the maze has moved to Blue Toad Hard Cider. The 2024 season is Sept 21. - Nov 3. Enjoy the corn maze, night maze, live music, and private campfires in Nelson County!