October is one of the best times to visit Hampton, VA. The weather turns cooler, summer crowds ease, and the calendar fills with festivals, campus traditions, waterfront events, live entertainment, and Halloween experiences.
Plan a weekend, or stay for the full month. These 10 October events give couples, families, friend groups, visiting alumni, and traveling professionals plenty of reasons to extend a Hampton trip.
October in Hampton at a Glance
- October 3: Racing at Langley Speedway and community events in Hampton
- October 8–11: Suffolk Peanut Fest
- October 10: Historic Phoebus Fall Festival and Downtown Hampton Second Saturdays Flea Market
- October 16–18: Fort Monroe Ghost Walk
- October 17–18: Town Point Virginia Fall Wine Festival in Norfolk
- October 18–25: Hampton University Homecoming
- October 24: Fleet Fest and Hampton CVB Halloween Speedfest
- October 24, 29, 30, and 31: Hampton Horror Tours
- Hampton Comicon: Check the official event calendar for confirmed 2026 dates
1. Hampton University Homecoming, October 18–25, 2026
Hampton University Homecoming is the centerpiece of the month for alumni, families, students, and visitors returning to the city. The official eight-day schedule includes concerts, the Miss and Mister HU Coronation, the NPHC Greek Step Show, the Pirates Vendors Bazaar, alumni events, a parade, tailgating, and the Homecoming football game.
The Hampton Pirates face Monmouth University on Saturday, October 24, at 2 p.m. at Armstrong Stadium.
Review the complete Hampton University Homecoming schedule before you arrive. Several events are ticketed, while others are free and open to the public.
Best for: Visiting alumni, friend groups, college football fans, and families planning a spirited fall weekend.
2. Hampton Comicon, Check the Official 2026 Schedule
Hampton Comicon is a family-friendly comic convention held at the Hampton Roads Convention Center near the Coliseum district. Expect comics, collectibles, exhibitors, artists, costumes, and a lively cosplay community.
The event is commonly associated with a mid-October weekend, including the October 17–18 window. However, the official Hampton Comicon website had not published confirmed 2026 dates at the time of writing. Verify the schedule, tickets, exhibitor information, and cosplay details through the official Hampton Comicon site.
Staying nearby makes it easier to attend panels and return home between activities. Choose a home with free parking, a full kitchen, and room to relax after a busy convention day.
Best for: Families, comic fans, cosplayers, and groups visiting the Hampton Roads Convention Center.
3. Historic Phoebus Fall Festival: October 10, 2026
Head to neighboring Phoebus on Saturday, October 10, for one of Hampton’s signature fall street festivals. The Historic Phoebus Fall Festival takes over East Mellen Street with live music, handmade art, craft vendors, community exhibits, food trucks, and local beer and cider offerings.
The Visit Hampton event listing places the festival in Historic Downtown Phoebus, with activities scheduled from approximately 8 a.m. to 6 p.m. Check the listing before heading out for final timing and updates.
Arrive early for easier parking and time to browse the vendors before the afternoon crowds arrive. Afterward, explore Phoebus restaurants and nearby Fort Monroe.
Best for: Families, couples, shoppers, food lovers, and visitors who enjoy local culture.
4. Fort Monroe Ghost Walk, October 16–18, 2026
For a memorable October evening, join the Fort Monroe Ghost Walk from October 16 through 18. The Fort Monroe Authority describes this as an outdoor walking tour of approximately one hour and more than half a mile.
Tours begin at the Fort Monroe Visitor & Education Center, 30 Ingalls Road. The event runs rain or shine, so wear comfortable shoes and dress for changing evening temperatures. Guests under 18 must attend with an adult, and the tour is not recommended for children under 12.
Review the Fort Monroe Ghost Walk details and purchase tickets in advance. Availability may be limited during Homecoming weekend.
Best for: Couples, history enthusiasts, adult groups, and travelers looking for a distinctive Halloween experience.
5. Fall Town Point Virginia Wine Festival: October 17–18, 2026
Extend your Hampton stay into a weekend in Norfolk for the Fall Town Point Virginia Wine Festival. The 2026 festival is scheduled for October 17–18 at Town Point Park on the Downtown Norfolk Waterfront.
The event runs from 11 a.m. to 6 p.m. each day. Wine sampling ends at 4:30 p.m., and wine sales end at 5 p.m. In addition to Virginia wines, expect waterfront views, live entertainment, food, and a relaxed fall atmosphere.
Check the official Norfolk event information before traveling. Plan for heavier traffic and allow extra time for parking in Downtown Norfolk.
Best for: Couples, friend groups, wine enthusiasts, and adults planning a waterfront day trip.
6. Suffolk Peanut Fest, October 8–11, 2026
Suffolk Peanut Fest brings four days of family entertainment to Suffolk Executive Airport from October 8–11. The festival features concerts, amusement rides, contests, fireworks, a demolition derby, a peanut cup race, a motorcycle rally, and food vendors.
General admission is listed at $10 per person, with children 12 and under admitted free. Parking is free, but confirm ticket details and the daily schedule through the official Suffolk Peanut Fest website.
This is a strong choice for families who want a full day of activities without needing to plan multiple stops.
Best for: Families, groups, motorsports fans, and visitors who enjoy large community festivals.
7. Downtown Hampton Second Saturdays Flea Market: October 10, 2026
Stay in Hampton after the Phoebus Fall Festival and continue the evening at the Downtown Hampton Second Saturdays Flea Market. The October market is scheduled for 5–10 p.m. at Queens Way and Kings Way.
Shop local vendors, browse vintage finds, enjoy live music, and visit Downtown Hampton restaurants and businesses. The evening format makes this an easy addition to a full day of fall activities.
See the Downtown Hampton event calendar for updates and vendor information.
Best for: Shoppers, couples, families, and visitors who want to experience Hampton after dark.
8. Fleet Fest, October 24, 2026
Fleet Fest returns to Naval Station Norfolk on Saturday, October 24, from 10 a.m. to 5 p.m. The event is free and open to the public, with entry through Gate 2.
Fleet Fest offers a close look at Navy life and maritime operations. Because it takes place on an active military installation, bring required identification and follow all official entry instructions. Review the City of Norfolk’s Fleet Fest listing before you go.
Fleet Fest falls on the same day as Hampton University’s Homecoming football game and Halloween Speedfest, making October 24 one of the busiest event days of the season.
Best for: Military families, children, visitors interested in maritime history, and patriotic events.
9. Hampton CVB Halloween Speedfest, October 24, 2026
Hampton’s 2026 Halloween Speedfest is scheduled for October 24 from 6–9 p.m. at Larry King Law’s Langley Speedway, not Hampton Coliseum.
The race-night program includes VA Sprints, Limited Late Models, VA Mini Cups, and Southern Ground Pounders. Check the Langley Speedway schedule for tickets, entry details, and any updates.
Plan this event after daytime activities such as Homecoming, Fleet Fest, or a waterfront walk. Expect traffic near the speedway and arrive early if you want time to park and settle in.
Best for: Motorsports fans, families with older children, and groups seeking high-energy entertainment.
10. Hampton Horror Tours: October 24, 29, 30, and 31, 2026
Hampton Horror Tours offers a 60-minute guided walking experience through historic Downtown Hampton. Tours depart from the Hampton History Museum at 6:30 and 8 p.m. on October 24, 29, 30, and 31.
Expect eerie stories from Hampton’s past, historic sites, and a stop near the St. John’s Church graveyard. The tour is not recommended for children under eight. According to the city and museum information, advance tickets are $18 for adults, with child pricing available for ages 8–12.
Review the latest details through the Hampton History Museum before booking. Comfortable walking shoes are essential.
Best for: Couples, history lovers, adult groups, and Halloween fans.
Plan Around the Crowds
Homecoming and convention weekends can fill Hampton lodging early, especially when major events overlap. Book as soon as your dates are firm, and confirm event tickets before finalizing your itinerary.
Use these practical tips:
- Reserve lodging several weeks ahead for October 17–25.
- Allow extra driving time across Hampton Roads during event weekends.
- Check venue parking rules and entry requirements in advance.
- Use a designated driver or rideshare for wine festivals and evening events.
- Build flexibility into your schedule for traffic, parking, and event lines.
- Choose accommodations with dedicated parking so you can leave your car at home base.
- Check official event websites before departure for schedule changes or weather updates.
Stay Longer in a Hampton Home
A hotel room works for a quick overnight visit. A fully furnished home works better when your plans span several days, or several weeks.
Cornerstone Cottages offers fully furnished Hampton homes with space to spread out, free parking, and the comforts of home. Cook tailgate meals and post-festival dinners in a professional-grade kitchen with full-size appliances, quality housewares, and generous prep space. Gather around an outdoor fire pit, relax in a game room, or unwind in a jacuzzi tub, depending on the property you choose.
For extended trips, our extended-stay options support 29–90 day visits with No Lease/Flexible Lease/Month to Month arrangements. That makes Cornerstone Cottages a practical choice for seasonal travelers, visiting alumni, relocating guests, and traveling professionals who need reliable Corporate Housing with quiet comfort and move-in-ready convenience.
Whether you are booking a weekend of events or a full October stay, choose a Mid-Term Rental in Hampton, VA that gives you more space, privacy, and flexibility than a hotel.
Check Cornerstone Cottages availability and find your Hampton home for fall.