Fall flies by so quickly, and before you know it, you’ve missed all the seasonal fun Virginia Beach has to offer. In Virginia Beach not every fall activity feels just like FALL but there are still so many things to enjoy that only happen in the fall. Every year I think I’m going to really enjoy the Fall activities but between the time it takes to research them and plan them into my schedule it often falls through. This year I’m not letting that happen and I’ve made a list of all the Fun Fall Activities in Virginia Beach and a touch beyond.

When planning your autumn outings here, remember: the best time to visit many outdoor spots is mid- to late October, when the air is cooler, and mornings and evenings show off with that soft fall glow. Crowds tend to be lighter earlier in the week, and doing a short outing in the morning or just after school can catch that better light. These moments—walking through a farmers market, picking apples at the farm, or visiting local festivals—are where memories happen

Visit a Pumpkin Patch

A pumpkin patch experience is a quintessential Fall Activity in Virginia Beach and often includes more than just choosing a pumpkin. Expect hayrides, corn mazes, little petting zoos, seasonal treats like cider, donut stands, or pumpkin-spiced goodies. It’s a family activity that has something for everyone from your littles to you —the novelty, the nostalgia, and those sweet pumpkin patch photo opportunities. Click here to join the email list and get my guide to taking better cell phone photos to make the most of the photo opportunities that abound.

Best Local Pumpkin Patches

Cullipher Farm – 772 Princess Anne Road, Virginia Beach.

Their U-pick pumpkin field starts around September 20 and they have a fun, free play area for the little ones. There is so much to do including pick your own apples, all the cute farm animals, sweet treats like apple cider slushies and homemade ice cream and for your older kids try their corn maze.

Hunt Club Farm’s Harvest Fair – 2388 London Bridge Road, Virginia Beach.

A Virginia Beach classic, Hunt Club Farm has so much to do and see. Enjoy the Pumpkin Patch, Petting farm, tree-walk adventure.  The Harvest Fair is great for a fun fall family outing even if the weather doesn’t feel like fall and even better there are plenty of opportunities to fit this one into your schedule, it runs from September 27 to November 2.

Virginia Beach Farmers Market – , 3640 Dam Neck Rd, Virginia Beach.

Find lots of pre-picked pumpkins, including mini pumpkins, pie Pumpkins and gorgeous heirloom pumpkins and shop for beautiful fall produce and yummy fall themed bakery treats and ice cream from vendors throughout the farmers market. Try their Harvest Festival on October 11th with craft vendors and food trucks.

Explore Outdoor Trails & Nature Walks

While Virginia Beach isn’t known for dramatic leaf color, some trails and parks still offer beautiful greenery, crisp air, shady paths, and wildlife during fall. Walking these trails is the perfect fall activity in Virginia Beach to gives time to slow down, chat, and create small moments to connect.

Top Trails & Parks for Outdoor Walks

Tidewater Arboretum – 1444 Diamond Springs Rd.

Tucked away off one of VB’s main roads, is a small arboretum with theme gardens, with nice short paths for little legs. These are easy walks and a fun simple outing for families.

First Landing State Park  – 2500 Shore Dr, Virginia Beach

While Virginia Beach isn’t always loud with fall color, the trails at First Landing offer nice forest walks, shoreline views, picnic areas, and good trails options for everyone. A good trail option for the little ones who like to walk themselves or will want to be carried  is the Bald Cypress Trail Loop; it’s about 1.5 miles.  (You might want to check current park access ahead of time.)

Mount Trashmore Park – 310 Edwin Dr, Virginia Beach

With large open lawns for running, playgrounds, and a lake trail Mt. Trashmore is a great spot for fall play time even when it’s finally not terribly hot outside. Try a family walk around the lake, flying a kite, or bringing a picnic lunch to enjoy after running around on the playground.

Tips for Trail Walks

• Dress in layers; mornings can be cooler, afternoons warm.
  
• Shoes that grip—leaves or dew might make paths slippery.
  
• Bring snacks, water, even a magnifying glass or simple scavenger hunt for kids (a leaf, a pinecone etc.).
  
• Go early or later in the day for softer light if you’re hoping for photos.

Attend a Fall Festival or Fair

Festivals are where community energy meets seasonal fun—the food, the music, the crafts—they all connect us and give kids so much wonder and are a family favorite anytime I talk to clients and friends about fall activities in Virginia Beach.

Local Festival Picks

Neptune Festival Boardwalk Weekend –September 27th & 28th

A Virginia Beach Staple for over 50 years this fun festival happens in the Fall but does things the coastal community way. Instead of trying to make Fall in Virginia Beach something its not we have fun in the Fall with multiple free concerts on the ocean front stages, a must see sandsculpting competition ($7 per person) that will have your kids feeling like they’ve stepped into a dream world, two art shows including the youth art show, a surfing competition, Dock, Dogs, and so much more there is plenty of family-friendly entertainment, and delicious food from local food vendors to enjoy.

Autumn in the Air (Mount Trashmore) – Saturday, November 1st, 12:00pm-5:00pm

A one-day outdoor festival with music spanning the genres of Folk, Americana, and Rock, local vendors featuring handcrafted goods and local treats. There are fun fall activities for all ages from Pumpkin bowling to bounce houses, rock climbing and more. I’d be surprised if your teenager or threenager couldn’t find something to enjoy! This is a great Virginia Beach fall activity for families with children who may need some space from all the excitement as they will be including a sensory zone.

Quick Festival Tips

• Bring portable chairs, water, sunscreen—even in “fall,” sun still matters.
  
• Bring snacks and drinks for picky eaters
  
• Know parking well and arrive a bit early

Additional Popular Fall Activities in Virginia Beach

Here are a few more to round out your family’s fall activities in Virginia Beach bucket list:

• Visit Apple Orchards — Enjoy U-pick apples or just wander orchard rows at Cullipher Farms to enjoy a must do fall activity in Virginia Beach.
  
• Outdoor Fall Markets — Keep an eye on Virginia Beach market pages for local craft markets that pop up for fall, where you can shop, grab seasonal treats, and enjoy local artisans.
  
• Scenic Drives — A drive along the coastline, or to coastal farmlands to enjoy cooler air and wide views is a fun fall activity in Virginia Beach.

Fall Day Trips Worth the Drive

While plenty of family friendly fall activities here in Virginia Beach, there are a few special experiences just a short drive away that make for unforgettable fall memories. If you’re up for a day trip, these destinations are so worth the extra time in the car.

Colonial Williamsburg: Historic Charm with Fall Decor & Carriage Rides

Colonial Williamsburg in the fall is as picturesque as it is memorable. Starting in mid-October, the streets are decorated with subtle seasonal details, and the Fall color starts to emerge making the historic buildings and cobblestone paths feel even more inviting. It’s free to stroll through the Historic Area, enjoy the ambiance, and peek into shops along Duke of Gloucester Street. If you’d like to step inside the homes, taverns, and museums, tickets are required.

One of the most memorable ways to experience Williamsburg in autumn is with a carriage ride. Wrapped in a blanket, you’ll clip-clop down the same streets walked centuries ago by our founding Fathers, (a touch of romance for Mom and Dad, George Washington and Martha walked these very streets while they were courting), Enjoy stories, gardens, and architecture at a slower pace. And don’t miss The Cheese Shop—a local institution where my family always stops for sandwiches!

Tips: Mid-week visits are quieter, and mornings tend to be cooler and less crowded. Plan ahead for ticketed experiences if you want to go inside historic sites. Layers are helpful for carriage rides or longer strolls, as October days can still shift quickly.

King Family Vineyards & Roseland Polo: A Scenic Polo Match Picnic

For something different, head west toward King Family Vineyards in Crozet, VA, where fall Sundays are reserved for Roseland Polo. Matches run through the last weekend of October, with gates opening at 10:00 AM and play beginning around noon and entry is free. Families bring blankets, chairs, and picnics, you can make this outing as relaxed or elevated as you’d like. If you are like me you love a good reason to elevate an outfit and make the occasion feel even more exciting. Food trucks and wine are available onsite, and the Blue Ridge backdrop sets the tone for a slow, scenic fall afternoon.

Tips: Arrive early to snag a good spot near the field. Polo is family-friendly, but bring shade or an umbrella if it’s sunny, and pack your favorite picnic staples to make it an experience. Check schedules the morning of—matches can occasionally shift with weather.

What to Wear for Fall Activities

Layering & Comfort

Because weather shifts quickly here, layering is key. Think lightweight jackets, sweaters, breathable shirts.

Activity-Specific Tips

• Trails: closed-toe shoes, possibly boots if muddy. Hats/sunglasses. Dress kids in layers you can wash.
  
• Festival Days: comfy shoes, easy outfits for layering, a small bag with essentials (snacks, wipes).
  
• Pumpkin patches/corn mazes: Cute but practical outfits you don’t mind getting dirty and always layers, they are a Virginia Beach necessity.

Don’t Forget…

• Water, snacks, bug spray (we don’t get cold snaps to get rid of the bugs until later in the season ).
  
• Cash or card for parking fees.
  
• A blanket or sheet if you want picnic or sit outside.
  
• A camera (or phone) for spontaneous moments—it’s often the photos of the in-between moments that become favorites.
  

Make the Most of Fall Activities in Virginia Beach

Fall may arrive a little slowly here, but the moments it offers are full of fun and memories ready to be made. Whether it’s choosing pumpkins, exploring trails, enjoying local festivals, or making the drive for a day trip—these experiences are all about slowing down and being together.

What I love most about fall in Virginia Beach is how our familiar sand, breeze, green trees and gorgeous sunshine shifts just enough to feel new. It’s in those in-between weeks, the golden mornings, the porch coffees, the quiet walks, and the fun outings that I find beauty in time with my family and friends.

Which of these Virginia Beach fall activities is at the top of your family’s fall bucket list? Leave a comment below—I’d love to hear your favorite hidden gem or tradition.

Also, if you’re thinking about adding family portraits to your fall bucket list, let’s chat! Fall Family sessions fill up fast and I have a handful of evenings left for gorgeous fall light filled sessions.