Chester Family-Friendly Fall Activities 2026

Get ready for a spooktacular Halloween celebration! This family-friendly event invites everyone to don their most creative costumes for a chance to win. Enjoy an evening filled with music, delicious food from vendors, exciting bounce houses, and other surprises. It's...

Gallmeyer Farms invites families for a traditional fall experience at their beloved Pumpkin Patch. Visitors can wander through fields to pick their own pumpkins, choosing from a wide selection of sizes and varieties. The event offers complimentary hayrides, a fun...

Step into a world of enchantment at Garden Glow, where Maymont transforms into a mesmerizing spectacle of light after dark. Wander through a mile-long pathway illuminated by breathtaking installations from international artists, featuring dancing lights synchronized to music, towering floral...

Celebrate fall at the Scott's Addition Pumpkin Festival! This vibrant event features live music, a thrilling costume contest for all ages (including pets!), and a dedicated kids' area with expanded activities. Enjoy a variety of food and drinks while soaking...

Join Shalom Farms for their annual Harvest Festival, a celebration of the season with a focus on community and healthy food. This family-friendly event offers a delightful evening with a delicious family-style meal, cozy fire pits for s'mores, and live...

Celebrate the harvest season at Lewis Ginter Botanical Garden's HarvestFest. This family-friendly event features live music, creative seasonal crafts like pumpkin painting, and delicious fall-themed food options. Discover educational demonstrations and enjoy a day of nature's bounty.

Embrace the autumn spirit at Chesterfield Berry Farm's Fall Festival & Pumpkin Harvest. Explore a vast pumpkin paradise, get lost in their famous 8-acre corn maze, and enjoy numerous farm-tastic activities. It's the perfect place to create lasting fall memories...

Ashland Berry Farm invites families to its 30-acre pumpkin patch for a quintessential fall experience. Enjoy a scenic hayride to pick your own pumpkin, or opt for the 'All-You-Can-Carry Pumpkins' challenge. As dusk falls, the farm transforms into Terror on...

Discover Pumpkinville, a charming seasonal attraction in Toano, VA, offering a delightful fall experience for the whole family. Pick your perfect pumpkin from their extensive patch or selection, and immerse yourselves in a festive Halloween atmosphere. Enjoy complimentary activities like...

Discover the magic of fall at Holly Fork Farm's annual pumpkin patch and festival. Families can enjoy a classic hayride to pick out pumpkins, explore a fun corn maze, and launch pumpkins. Kids will love visiting the farm animals and...

Newport News Fall-O-Ween Festival is a vibrant, two-day celebration of autumn and Halloween. This family-friendly event features a bustling marketplace with crafters and themed vendors, live entertainment, and a dedicated seasonal beer garden. Attendees can enjoy a variety of food...

Experience a unique Halloween tradition at the Night of the Living Museum! This family-friendly event invites visitors to explore the museum's galleries and outdoor trails, collecting candy from multiple stations. Enjoy themed activities, meet fascinating creatures, and be entertained by...

Celebrate autumn at The Mariners' Park Fall Festival! This family-friendly event features pumpkin decorating, live music, and a delightful Teeny Tiny Farm. Adults 21 and over can enjoy beer and cider tastings from a variety of local breweries and cideries,...

Discover a harvest of fun at Belmont Pumpkin Farm, celebrating over 40 years of fall family traditions. Explore sprawling pumpkin patches, get lost in a thrilling corn maze, and enjoy scenic hayrides. Indulge in delicious farm-smoked BBQ, street tacos, and...