Fall has officially arrived in Coastal Virginia, and if you ask me, October is one of the best months to get out and explore everything our area has to offer. The temperatures are finally cooling down, festival season is in full swing, and there’s no shortage of family-friendly events, outdoor adventures, and Halloween fun.

Whether you’re new to the area or you’ve called Hampton Roads home for years, here’s your guide to some of the best October events happening around Virginia Beach, Chesapeake, and Norfolk.

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Virginia Beach Events

Virginia MOCA Boardwalk Art Show

October 2–4, 2026

One of the region’s signature fall events returns to the Oceanfront with hundreds of artists from around the country showcasing paintings, photography, jewelry, ceramics, sculpture, and more. It’s the perfect opportunity to support artists while enjoying beautiful weather by the ocean.

Great for: Art lovers, families, and anyone looking for unique gifts.

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Hunt Club Farm Fall Harvest Fair

Select Dates Throughout October

Pumpkin patches, hayrides, farm animals, giant slides, bonfires, food vendors, and plenty of activities for kids make this one of the area’s favorite fall traditions.

Don’t miss: Picking out the perfect pumpkin and enjoying fresh apple cider.

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Haunted Hunt Club Farm

Evenings Throughout October

For those looking for something a little scarier, Hunt Club Farm transforms into one of Coastal Virginia’s premier haunted attractions featuring haunted hayrides, spooky trails, and terrifying haunted houses.

Best for: Teens and adults looking for Halloween thrills.

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Neptune’s Fall Wine Festival

October 10–11, 2026

Sample wines from Virginia and beyond while enjoying live music, food vendors, and beautiful oceanfront views.

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Chesapeake Events

Hickory Ruritan Club Corn Maze

Weekends Throughout October

A Chesapeake tradition! Families can explore the giant corn maze, enjoy hayrides, pumpkin patches, games, and delicious local food.

It’s one of my favorite ways to celebrate fall close to home.

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Great Bridge Pumpkin Festival

Mid-October

Celebrate Chesapeake’s agricultural roots with pumpkins, craft vendors, live entertainment, food trucks, kids’ activities, and plenty of seasonal fun.

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Chesapeake Arboretum Fall Festival

October 2026

Take a stroll through beautiful gardens while enjoying local vendors, nature activities, educational exhibits, and family entertainment.

Perfect for enjoying the beautiful fall weather.

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Norfolk Events

Norfolk Harbor Half Marathon & 5K

October 2026

Whether you’re running or cheering from the sidelines, this popular race offers scenic waterfront views through downtown Norfolk.

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Norfolk Botanical Garden’s Garden of Lights Preview Events

Late October

As the holiday season begins to approach, the Botanical Garden starts preparing for one of Hampton Roads’ most beloved traditions with special seasonal programming.

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Ghent Fall Festival

October 2026

Enjoy local artists, food trucks, live music, shopping, and community fun in one of Norfolk’s most charming historic neighborhoods.

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Why I Love Fall in Coastal Virginia

One of the best parts of being a REALTOR® isn’t just helping people buy and sell homes—it’s helping them fall in love with the communities they call home.

Whether you’re spending the afternoon walking the Virginia Beach Boardwalk, getting lost in a Chesapeake corn maze, or enjoying a festival in Norfolk, these local events are what make living here so special.

If you’re thinking about buying or selling a home this fall, I’d love to help you discover not just the perfect house, but the neighborhood and community that fits your lifestyle.

Have a wonderful October, and I hope to see you out enjoying everything Coastal Virginia has to offer!

Happy Fall!

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Looking for a Home in Coastal Virginia?

Whether you’re searching in Virginia Beach, Chesapeake, Norfolk, Suffolk, or anywhere in Hampton Roads, I’m here to guide you every step of the way.

Let’s find a place you’ll love to call home.