November Cypress Creek Events
Gather. Give Thanks. Enjoy the Feast.
Wine Tasting Event
November 14th: Join us in Cypress Creek for a Wine Tasting!
For more information contact admin@ccgcsmithfield.com
Turkey Trot
November 27th: Join us in Cypress Creek for the annual post-feast Turkey Trot! Visit the Cypress Creek HOA for more information!
For more information contact admin@ccgcsmithfield.com
Windsor Castle Walking Tour
Step back in time and discover how Windsor Castle has witnessed the making of Smithfield—from its pre-colonial roots to its vibrant present day. Join us for a guided walking tour that brings centuries of history to life.
📍 Meet: On the grounds near the house, 301 Jericho Road, Smithfield.
Pickers Market
Hunt for hidden gems and one-of-a-kind finds at Downtown Smithfield’s Pickers Market!
Held on the second Saturday of each month, April through November, this beloved event transforms the Smithfield Visitor Center parking lot (behind When Pigs Fly, 315 Main St.) into a treasure hunter’s paradise.
🕘 Hours: 9:00 a.m. – 1:00 p.m.
💲 Admission: Free
Join your neighbors, browse vintage goods, antiques, and collectibles — and enjoy the thrill of the hunt!
📄 Vendor applications are available under the Files tab above.
📞 For more information, call 757-365-1644 or email cchapman@isleofwightus.net
Mistletoe Market
Plan to celebrate the season with family and friends at the annual Mistletoe Market in downtown Smithfield! Held on Saturday, November 22, 2025 (always the Saturday before Thanksgiving), this festive evening along the 100–300 blocks of Main Street will feature 75+ vendors, artists, and crafters offering handcrafted and unique items, plus food, live music, a cocktail garden, carolers, and Santa himself. Enjoy performances by Studio Seventeen (2–2:30 pm), Southside Ballet (3–4 pm), Footnotes School of Dance (4:30–5 pm), and the Smithfield High Choraliers (5:30 pm). Visit Santa from 2:30–6:30 pm at Perfectly Natural Soap, 202 Main Street. Free shuttle service runs 2–7 pm with parking at Windsor Castle Park next to Kayak Lane. Admission is free—come enjoy holiday magic on Main Street!
