Best Bets

Franklin Farmers Market

Franklin’s Market on Main is where you will find fresh, local produce and specialty items from vendors around the community..

When: Saturday year round & Wednesday from April – November

Time: Saturday 9am – Noon / Wednesday 4pm – 7pm

Location: 210 South Main St. Downtown Franklin

Christmas Craft Fair

Get into the holiday spirit and get an early start on your Christmas shopping during this craft fair sponsored by the Woman’s Club of Windsor. Enjoy a large selection of vendors, bake sale, raffle, along with breakfast and lunch.

Date: November 4,  2023

Time: 9am – 3pm

Location: Windsor Town Center

Holiday Open House

Downtown Franklin invites you to the annual Holiday Open House and Craft Fair. Come and shop with downtown businesses, enjoy craft vendors, music, the Farmer’s Market, food trucks and more!

Date: November 11,  2023

Time: 10am – 3pm

Location: Historic Downtown Franklin

Holiday Vendor Fair

This vendor fair will feature crafters, commercial vendors and food vendors.All proceeds benefit the Courtland Volunteer Rescue Squad.

Date: November 11,  2023

Time: TBA

Location: Southampton Ag & Forestry Museum | 26315 Heritage Lane | Courtland, VA

Wakefield Tree Lighting

Ring in the Christmas season at the Wakefield Community Tree Lighting Ceremony. Enjoy pictures and a visit with Santa after the tree lighting

Date: November 30,  2023

Time: 6:30pmm

Location: Wakefield Foundation | Wakefield, VA

Franklin Christmas Parade

Ring in the Christmas season at the annual Franklin Christmas Parade. This year’s theme is “Candy Cane Lane”! If your group or organization would like to enter a float, call 757-562-2475 or email [email protected]

Date: December 1,  2023

Time: 7pm – 9m

Location: Main Street | Franklin, VA

Holiday Toy Ride

Help bring a smile to a child’s face by donating a new toy at either Suffolk Walmart location for the Suffolk Sheriff’s Office Holiday Toy Drive. For more information, call 757-514-7840.

Date: December 2,  2023

Time: 10am – 3pm

Location: Walmart | 1200 N. Main Street | Suffolk, VA

Courtland Christmas Parade

Date: December 9,  2023

Time: 1pm

Location: Main Street | Courtland, VA


Isle of Wight Parks and Rec presents this all-inclusive holiday event featuring holiday activities, music and dancing, breakfast for dinner and a visit by Santa!

Date: December 15,  2023

Time: 5pm – 8pm

Location: Windsor Town Center | Windsor, VA