Fall Festivals in Cumberland Valley: Your Guide to the Best Autumn Events

There is no shortage of Fall events in the Cumberland Valley. Whether you’re here for the arts, seasonal treats, live music, or just to soak in the beauty of the season, our region offers a festival for everyone.

From quaint downtown streets lined with artists and vendors to vibrant sunflower fields bursting with golden blooms, September and October are filled with celebrations that capture the heart of autumn in Pennsylvania.

If you’re planning a September or October getaway, here’s your guide to some of the best fall festivals in the Cumberland Valley, all within an easy drive of Pheasant Field Bed and Breakfast.

Harvest of the Arts – Carlisle

Date: September 27th, 2025

Fall festival craft fair

One of Carlisle’s signature events, Harvest of the Arts transforms downtown into a vibrant open-air gallery. Over 100 artists and craftsmen line the streets, offering everything from fine art to handmade jewelry. Stroll through the exhibits, enjoy live music, and sample delicious food from local vendors. It’s a celebration of creativity that perfectly captures the spirit of fall in our charming town.

New Cumberland Apple Festival – New Cumberland

Date: September 27, 2025

Celebrate autumn’s favorite fruit at the New Cumberland Apple Festival, where you can indulge in apple pies, dumplings, cider, and other seasonal treats. Beyond the food, you’ll find handmade crafts, live entertainment, and activities for the whole family. It’s a sweet slice of small-town Pennsylvania charm.

wagon of apples with girl smiling

Pennsylvania Tea Festival – Mechanicsburg

Date: September 19-20, 2025

china teapot

Located at the Rosemary House & Sweet Remembrances, tea lovers, this one’s for you! The Pennsylvania Tea Festival offers tastings of specialty teas, informative workshops, and a marketplace of unique tea-related products. Whether you’re a dedicated tea drinker or just curious, it’s a relaxing and flavorful way to spend a fall afternoon.

Sunflower Festival at Meadowbrooke Gourds – Carlisle

Date: September 27-28, 2025

Just a short drive from our B&B, Meadowbrooke Gourds invites you to wander through fields of golden sunflowers in full bloom. The festival also includes free pick-your-own flowers, seasonal crafts, gourd-decorating activities, and delicious local food. It’s a photographer’s dream and a beautiful way to enjoy the last warm days of summer as fall begins.

Meadowbrooke Gourds Sunflower Festival

Other Great Fall Festivals in the Cumberland Valley

Fall Furnace Fest – Pine Grove Furnace State Park

Date: October 18-19, 2025

Step back in time at Fall Furnace Fest, held at historic Pine Grove Furnace State Park. Learn about the area’s iron-making history, watch live demonstrations, and browse local craft and food vendors. With scenic hiking trails nearby, it’s the perfect spot to combine a little history with the natural beauty of fall foliage.

Pennsboro Pumpkin Fest – Enola

Date: October 11-12, 2025

Pumpkins, pumpkins everywhere! At Pennsboro Pumpkin Fest, you can browse pumpkin-themed crafts, sample pumpkin-flavored treats, and enjoy family-friendly games and activities. It’s a festive, colorful way to embrace the harvest season.

Shippensburg Beer and Wine Festival – Shippensburg

Date: September 20, 2025

Raise a glass at the Shippensburg Beer and Wine Festival, where you can sample from a wide selection of local breweries and wineries. Pair your drink with tasty bites from food trucks, enjoy live music, and soak up the friendly festival atmosphere.

Make Pheasant Field B&B Your Fall Getaway

With so many events happening across the Cumberland Valley, you’ll want a comfortable, welcoming home base for your adventures. At Pheasant Field Bed and Breakfast, you can start your morning with a hearty homemade breakfast, spend the day exploring festivals, and return to relax in peaceful countryside surroundings.

Plan your fall getaway now and experience the best that our region has to offer. Whether you’re coming for a favorite festival, a romantic weekend, or just to soak up the autumn colors, we’d love to host you.

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