On Thanksgiving night, the drive-through loop around Chesapeake City Hall lights up for the first time this year and stays lit nightly until January 2. By then, at 700 Conference Center Drive, more than 90 crafters will already have packed up from the city's holiday craft show the weekend before.
Chesapeake's 2026 city holiday calendar is built around two addresses: 306 Cedar Road and 700 Conference Center Drive. Even the Rotary parade, which starts out on Battlefield Boulevard, finishes in front of City Hall. The Cedar Road events run outdoors, at night and for weeks. The Conference Center hosts the indoor events, which each last a day or a weekend. If you know which events belong to which address, you can plan all six weeks of the season without opening a dozen browser tabs.
The season, date by date
| Date | Event | Address | Cost |
|---|---|---|---|
| Sat. Nov. 21 and Sun. Nov. 22 | Chesapeake Holiday Craft Show | 700 Conference Center Drive | Free admission and parking |
| Nov. 26 through Jan. 2 | Deck the Hall drive-through lights | 306 Cedar Road | Free |
| Sat. Dec. 5 | Holly Jolly Jog, then the 43rd Chesapeake Rotary Christmas Parade | Battlefield Boulevard to Cedar Road | Free to watch; registration for the jog |
| Fri. Dec. 11 | City Holiday Luncheon | 700 Conference Center Drive | $15 residents, $20 nonresidents |
| Sat. Dec. 12 and Sat. Dec. 19 | Fa La La Land | 306 Cedar Road | Free |
| Thu. Dec. 17 | Holiday Brass Concert | 700 Conference Center Drive | Free |
The table shows the pattern. The Conference Center opens the season in November and adds two indoor stops in mid-December, on the 11th and the 17th. Cedar Road hosts everything you can do from a car or a curb.
Conference Center Drive starts the season indoors
The Chesapeake Holiday Craft Show is the first event on the calendar, two weekends before December. Hours are 10 a.m. to 5 p.m. on Saturday, November 21, and 11 a.m. to 4 p.m. on Sunday, November 22. Admission and parking are free. The city's event listing describes more than 90 crafters selling handmade gifts and decorations, along with Santa's Workshop, face painting, train displays, Santa appearances, mascot photos and concessions. The show closes four days before Thanksgiving, which makes it the last city event before the Cedar Road lights come on.
In December the Conference Center hosts two more events, each a single date:
- The City Holiday Luncheon runs Friday, December 11, from 11 a.m. to 1 p.m. Tickets are $15 for residents and $20 for nonresidents, and registration goes through the city's event page.
- The Holiday Brass Concert is Thursday, December 17, at 6 p.m. It's free, and the city lists it as a performance by Virginia Symphony Orchestra brass players.
If you want to eat out before or after either one, there may be a new option nearby. The Virginian-Pilot reported in August that Mason's Famous Lobster Rolls was set to open its first Chesapeake location on August 19 in Greenbrier MarketCenter at 1220 Greenbrier Parkway.
Cedar Road has the events that run for weeks
The Conference Center events each last a day or a weekend. The City Hall events run for weeks. Deck the Hall is a free drive-through display that Chesapeake Parks, Recreation and Tourism lights from Thanksgiving Day through New Year's Day. Visit Chesapeake lists it as running daily from November 26, 2026, through January 2, 2027, from dusk to 10 p.m. That's more than five weeks of evenings. You can drive the loop on any weeknight after dinner without planning around a single date.
On two Saturdays the loop also gets a walking event. Fa La La Land runs December 12 and December 19, from 5 to 9 p.m., on the same grounds. The listing promises baby goats in holiday sweaters, carolers, face painting, holiday-themed food trucks, live ballerina performances on stage, and photos with roaming characters including a glass man, a stilt walker and Santa. Parking around the City Hall municipal center is free.
You can drive the lights any night, but you can only walk Fa La La Land on those two Saturdays. If you want both in one evening, drive the loop and then park for the walk on December 12 or 19.
December 5 closes Cedar Road for five hours
The 43rd annual Chesapeake Rotary Christmas Parade changes how the Cedar Road area works for one evening. This year's theme is "America250: A Christmas Celebration," marking the country's 250th anniversary, and Chesapeake Regional Healthcare is the presenting sponsor. The route starts at Mount Pleasant Road and Battlefield Boulevard and ends in front of City Hall on Cedar Road. That means the parade ends on the same grounds where Deck the Hall has been running for nine nights.
The parade listing and the race page give this timeline for the evening:
- 4 p.m. Roads in and around the route close to all traffic until about 9 p.m. Hampton Roads Transit Bus Route 14 stops serving Cedar Road between Battlefield Boulevard and Albemarle Drive. Riders can board or get off at Cedar Road and Albemarle Drive or at Cedar Road and Pines of Warwick instead.
- 5 p.m. Holly Jolly Jog check-in opens at Great Bridge Community Church.
- 5:30 p.m. The one-mile jog starts on Mt. Pleasant Road outside TowneBank. Registration is on RunSignup.
- 6 p.m. The parade steps off.
- About 9 p.m. Roads reopen.
The listing says the easiest parking and good views are at the Municipal Complex behind the Central Library on Cedar Road, which will also have food vendors and portable restrooms. The Great Bridge Community Center at 212 Holt Drive will be open during the parade with restrooms, snacks and family activities.
The closure window starts two hours before the parade. If you live near the route or usually drive Cedar Road on Saturday afternoons, plan your errands to finish before 4 p.m. or wait until after 9 p.m.
Two things to check before you go
Greenbrier Farms trees. Historic Greenbrier Farms advertises cut-your-own Christmas trees on its website. In May 2025, WAVY reported that the farm would open to the general public only during its Christmas, strawberry and pumpkin seasons. Since public access depends on the season, check the farm's site for 2026 tree-season dates before you go.
The Deep Creek Bridge pattern. If you drive Route 17 over Deep Creek to reach the Cedar Road events, the bridge isn't laid out the way it was a year ago. A traffic shift in May 2026 moved eastbound Route 17 onto the new span, while westbound traffic stayed on the old bridge, DVIDS reported. That layout is temporary, and the replacement project isn't expected to finish until 2028. Before you head to the lights, check the current lane setup.
If this season has you thinking about whether next December will be in the same house, a number makes a good place to start. Conner and Company can give you a clear read on what your Chesapeake home is worth now, so you can make that decision before the busy months. Get Your Instant Home Valuation.
