‘The most wonderful time of the year” is near, and there are several Middlesex County-area events to kick off the holidays.
Urbanna celebrations
This Saturday, Dec. 6, experience “Enjoy the Christmas Spirit All Day” in Urbanna, capped by the Urbanna Hometown Christmas Parade. It’s been a holiday opening event for nearly 30 years. When the founder Lois Jean Brooks passed away after running it for 27 years, the town government became the organizer. Register for the parade at Urbanna.com or https://urbanna.com/parade/index.php.
Things get started at 4:30 p.m. with the lighting of the trees at the historic Lansdowne estate at 271 Virginia St. in Urbanna.
The Middlesex Volunteer Fire Department station, sometimes referred to as the “Urbanna firehouse,” with food prepared by firefighters, and vendors and music, will be set up nearby. The firehouse is at 330 Virginia St. in Urbanna. There will also be vendors on Cross Street. and the alpacas are returning to the mini park adjacent to the Middlesex County Woman’s Club at 202 Virginia St. in Urbanna. Choirs will sing in the business district before the parade.
Visit with Santa and Mrs. Claus in the firehouse after the parade.
Urbanna homes tour
Experience the spirit of the holiday season in the heart of Virginia’s river country at the 2025 Urbanna Holiday Home Tour, presented by Urbanna Main Street. The beloved annual event returns this Saturday, Dec. 6, from 11 a.m. to 4 p.m., inviting guests to step inside some of Urbanna’s most charming homes — each beautifully adorned for the holidays.
This year’s walking tour features five historic homes and two cultural landmarks, offering a rare opportunity to explore the town’s architectural gems and rich heritage. These include the Marble House, Atherston Hall, the Johnson Home, the Cove House, the Carter Home, James Mills Scottish Factor Store and Museum (featuring The Colonial Singers of Williamsburg from 1-2 p.m.) and Lansdowne.
Tickets are $40 plus tax per person and can be purchased online in advance and the day of the event at urbannamainstreet.com/events. Tickets can also be purchased in person at the event for $50 plus tax per person (cash only). Guests will check in at The Carter Home at 130 Watling St. to receive their event materials and begin the tour. Parking is available at Urbanna Baptist Church, 121 Watling St., Urbanna, and street parking throughout the town. This year’s event is a walking tour (no public transportation will be provided), and due to the historic nature of the homes, Urbanna Main Street cannot guarantee ADA access.
The Urbanna Holiday Home Tour is Urbanna Main Street’s largest fundraiser of the year, supporting projects that enhance the town’s vitality and visual appeal.
For information, visit urbannamainstreet.com/events.
Water View
On Friday, Dec. 5, around 6 p.m. the Upper Middlesex Volunteer Fire Department and Santa will be riding throughout the Water View community with Santa riding aboard the fire truck spreading cheer to all.
After making his tour of the neighborhood Santa plans to arrive at the Water View firehouse at 6:30 p.m. to visit with children. The street address is 4583 Water View Road.
There will be refreshments and children’s crafts. Firefighters will be on hand providing safety tips for the holidays.
Deltaville
Tickets are selling fast for the Dec. 12 Deltaville Community Association (DCA) cruise on Jackson Creek. The tickets are available at Hurd’s Hardware in Deltaville. Tickets are $10 each, cash or check, limit six per family.
Cruises will depart at 5, 6 and 7 p.m., rain or shine. All passengers must report to the DCA Center, 17147 General Puller Highway, at least 15 minutes before the time on their ticket to receive a boarding pass for the boat. Wagons will take cruisers to Deltaville Marina for their boat ride. This is not an event for folks of limited mobility or for the very young. Children weighing less than 50 pounds must provide an appropriate personal floatation device.
The DCA community center will open at 2 p.m. on Dec. 12 to receive entries for the cookie contest. All cookies for the judged contest must be in the building by 4 p.m. Cookies for the contest must be homemade by the entrant. Prizes will be $100 first, $50 second, $30 third, and $20 fourth. Cookies for the people’s choice award ($50) can come anytime during the afternoon or evening.
They need lots of cookies for the party and for another DCA event the following evening. Please bring cookies.
The Christmas party will start at 4:30 p.m. and requires no ticket. There will be free hot and cold cider as well as hot chocolate and free cookies, of course.
Call Raynell Smith for information about the contest at 804-815-3102 or call Gail Butler with questions about the Christmas party at 804-353-6465.
Tappahannock
“Golden Christmas Memories” is the theme of the fifth annual Winterfest event and 50th annual Christmas Parade in Tappahannock on Saturday, Dec. 6. The parade begins at 4:30 p.m.
From the festive marketplace to the dazzling parade, it’s a day of the holiday spirit in historic downtown Tappahannock where vendors will be set up from 1-7 p.m.
The Ugly Sweater Contest is at 3:30 p.m. and the parade begins at 4:30 p.m. The float registration fee is $30 per float.
Mathews
“Jingle on the Bay!” is the theme of the Mathews Christmas Parade on Saturday, Dec. 13, from 1-2:30 p.m. The parade runs from Thomas Hunter Middle School to Chesapeake Bank, going down Church St. to Main St. to Buckley Hall Road.
Winners will be chosen for the best entry in each of the following nine categories: Civic, Animal, Walking Unit, School, Commercial, Motorized, Church, Parade Theme, and Antique Vehicle. Visit with Santa at Sibley’s Store Visitor’s Center from 2:30-4 p.m.
Register for the parade by Dec. 5 through the Mathews County Visitors and Information Center (MCVIC) at 804-725-4229 or mathewsvisitorcenter@gmail.com. There is no entry fee.
The tree lighting is at 7 p.m. on Friday, Dec. 12, on the historic court green.
Gloucester
Get ready for a full day of holiday magic in Gloucester’s historic district with Gloucester’s Christmas and Holiday Parade and tree lighting from 3-6 p.m. on Saturday, Dec 6.
The event starts at 3 p.m. with the Christmas and Holiday Parade, when festive floats, marching bands, and holiday magic fill Main St.
Immediately following the parade, gather on the Historic courtyard for the Annual Tree Lighting, presented by the Cook Foundation, at 5 p.m. Watch as the community gathers to light the tree and officially welcome the season with sparkling lights and holiday spirit.
The events are presented by the Gloucester Parks, Recreation and Tourism Department.
Throughout the day, explore The Festival of Trees at Tucker Store Pocket Park, Gloucester Resource Council’s Common Ground, and Main St.’s “Holiday Open House,” featuring unique shopping, dining, and seasonal fun.
Main St.’s photos with Santa begin at 10 a.m.
Bring the whole family and experience the magic of Gloucester’s holiday traditions, all in one joyful afternoon.
Sign up online to be in the parade at gloucesterva.gov/civicrec.
West Point
The West Point Christmas Parade is set for Sunday, Dec. 7, at 1 p.m.
The parade lines up on Kirby St. before turning down Main St. and running right through the festive heart of “Christmas on the Town.”
One trophy will be awarded to the entry filled with the most holiday spirit while representing the parade theme.
Christmas on the Town is the Town of West Point’s annual holiday kickoff event hosted by the West Point Chamber of Commerce, with the parade sponsored by Dominion Energy. From noon to 4:30 p.m. visitors can enjoy the family-friendly atmosphere with live music, beverages, shopping, a parade, caroling, a Tree of Life Ceremony, and Santa and his helpers.
