The Cavalier's Holiday Season, Sorted by What Neighbors Can Walk Into

How much of the Cavalier Resort's holiday season can you use if you live in Bay Colony and never book a room? Almost all of it. The resort's holiday page runs through a long list of events, from Thanksgiving through New Year's Eve. Under each one is a different entry rule, and only one of those rules requires you to be staying the night.

There are four ways in. Some events have no ticket at all. Some take an OpenTable reservation. Some need a ticket bought ahead of time. One item, the carriage rides, is limited to overnight guests and residents. If you know which event falls into which group, you can plan most of the season from your own driveway.

This is also the first holiday season under new ownership. WHRO reported in June that the Historic Cavalier, the Oceanfront Marriott, Embassy Suites and the Cavalier Beach Club sold to Connecticut-based Wheelock Street Capital, with HEI Hotels & Resorts managing the complex. According to WHRO, Wheelock managing director Tim Hodes told Hotel Business the new owners look forward to "continuing to steward and build upon" the resort. WTKR reported in July that property filings for the sale totaled $174,075,858. The 2026 calendar shows the traditions continuing. Nearly every date below is a returning event.

The Main Events by How You Get In

The table leaves out the reserved holiday meals and the resort's New Year's Eve event, A Cavalier New Year, which are covered below. Two of the open events fall on the busiest dates. One is the Grand Illumination, and the other is a short Santa hour every Friday through Christmas Day. Everything else needs some planning, and the planning starts this week.

Sunday, Nov. 22 Is the Whole Season in One Day

On one Sunday, the Cavalier runs three events back to back, each with a different way in. Breakfast with Santa at Becca Restaurant & Garden runs that morning from 8:30 a.m. to 2 p.m. Santa's Holly Jolly Show follows at 3 p.m. in the Crystal Ballroom. The Grand Illumination starts on the Great Lawn at 5 p.m.

The resort sequences them on purpose. The Holly Jolly Show page tells families to head to the Great Lawn for the Grand Illumination after the show. Tickets are $30++ for adults and children 3 and up, free for children 2 and under, and must be bought online ahead of time. The ticket includes a Singing Santa performance, professional photos, a take-home holiday gift, and cookies and cocoa.

The lighting itself is free. The Grand Illumination page describes three oceanfront hotels and their grounds lit for the season, with Santa arriving, carolers, and dancers from Ballet Virginia's Nutcracker. After the countdown, the resort offers photos with Mr. and Mrs. Claus, hot chocolate, roasted s'mores, and holiday cocktails in The Raleigh Room. The event page says it is open to the public with no reservations needed. The holiday hub also links an Eventbrite RSVP, which you can use or skip.

The Grand Illumination page includes the line "Rideshare highly encouraged." The amenities page lists valet at the Historic Cavalier for $7 per day or $34 overnight. It doesn't say how parking works on a night when the lawn fills up. For Bay Colony households, the resort sits right next door, so getting there is a short trip.

Fridays at Five, Santa Is Outside

After the lighting, the open part of the season shrinks to one hour a week. From the day after Thanksgiving through Christmas Day, Santa sits in his sleigh outside The Historic Cavalier Hotel on Fridays from 5 to 6 p.m. The dates are Nov. 27 and Dec. 4, 11, 18 and 25.

The Photos with Santa page says no reservations or tickets are required. You stop by during those hours and take your own photos. The resort also says plainly that this is not a professional photo session. Families who want professional photos have two Santa options that come with them, the ticketed Holly Jolly Show and Breakfast with Santa.

The last date falls on Christmas Day itself. For anyone who wants a Christmas afternoon outing close to home, the sleigh is out from 5 to 6 p.m. that Friday.

Becca Is Where the Reservations Pile Up

Once you need an OpenTable reservation, nearly everything runs through Becca Restaurant & Garden.

Breakfast with Santa runs every Saturday and Sunday from Nov. 21 through Dec. 20, from 8:30 a.m. to 2 p.m. You order from Becca's regular brunch menu, and there's a holiday kids' buffet at $15 per child. After the meal, Santa poses for professional photos in The Raleigh Room Loggia. You book through OpenTable like any other Becca table, and there are no separate event tickets.

Winter Wonderland Igloos open sooner and stay much longer than anything else here. OpenTable lists the dinner seating from Nov. 11, 2026, through Feb. 28, 2027, at $125 per party. Each private heated igloo seats two to six guests and comes with a toast, an amuse-bouche, a keepsake and a dedicated server. Dinner itself is ordered from Becca's à la carte menu. The resort's igloo page says rental fees vary by meal period, so $125 is the dinner-seating price, not a flat rate for every meal. There is also a Thanksgiving igloo on Nov. 26 only, at $200 per party plus a $95-per-guest prix-fixe menu.

Most holiday events end before New Year's. The igloos keep a reservable winter table on the property through February, the same months as the carriage rides.

The bigger holiday meals also need reservations. The resort lists Thanksgiving dining on Nov. 26, Christmas dining on Dec. 24 and 25, and New Year's Eve dining on Dec. 31. New Year's Eve also brings A Cavalier New Year, a Roaring Twenties-themed event that takes reservations, and Orion's Roof serves a four-course menu with live entertainment.

Two Ticketed Nights for Adults

The 8th Annual Virginia Bourbon Invitational is on the Cavalier Great Lawn on Saturday, Nov. 7, and its event page says general admission is sold out online. The holiday hub says tickets are no longer available to the public, and the remaining way in is a resort package. On that Saturday, the lawn is closed to anyone without a ticket or a package, the opposite of how it works two weeks later.

The second ticketed night is the Jingle Bell Jam on Thursday, Dec. 17, from 6 to 9 p.m. in The Raleigh Room. BJ Griffin, Chris Keys and friends perform live local holiday sets. Tickets are required, and attendees must be 21 or older. The event page doesn't list a price, so check it on the ticket link before you plan the evening.

The One Event You Can't Get Into

Only one item on the calendar is closed to the general public. The holiday page lists horse-drawn carriage rides through the resort grounds on select dates from December through February, with this restriction:

"Overnight resort guests and residents only."

The resort activities page says the same thing, naming overnight guests and Cavalier residents. Neither page explains what "resident" means or lists dates or a price. WTKR's coverage of the sale says 81 Cavalier residences were sold. If you aren't sure whether you count as a resident, ask the resort before you plan around a ride.

Even so, the carriages are visible from the public grounds. The resort's own gallery shows a carriage waiting at the hotel's main entrance. You can't ride without a room or residency, but you can see the carriages on any of those December evenings.

If Nov. 22 Doesn't Work

If the Cavalier's Sunday conflicts with your plans, another lighting comes six days later. Town Center's free Grand Illumination and Santa arrival is on Saturday, Nov. 28, from 5 to 6 p.m. at Fountain Plaza, 205 Central Park Ave. The Downtown Virginia Beach Partnership's event page says treats and hot chocolate will be available while supplies last. It lasts one hour, and the Cavalier's runs three. The Cavalier also schedules a show and a brunch on the same day.

For Bay Colony, the season starts on Saturday's sold-out bourbon lawn. The igloo bookings open the following Wednesday, Nov. 11. The free lighting is on Nov. 22, and the last walk-in Santa hour is the evening of Christmas Day.

Many Bay Colony buyers ask about the Cavalier next door, and living near a resort is part of what we talk through with every client. If you're thinking about a home where events like these are close by, Michael Rowland can show you how Bay Colony's location fits the way you want to spend your winters. Start your tailored market consultation.