West Point's holiday season opens in mid-October with a concert at Robinson/Olsson Auditorium. From there it moves to the pavilion at Riverwalk Park on Halloween, then to West Point Town Park the Saturday after Thanksgiving, then to a parade down Main Street on Dec. 6. After that, the town's decorated houses carry it through the rest of December. Two of the programs that run past the parade, the trolley rides and the decorated-tree auction, raise money for one Chamber scholarship.
Here's the season in order.
October Through December, Four Venues
- Saturday, Oct. 17, 7 p.m. Arts Alive opens its 2026–2027 concert series at Robinson/Olsson Auditorium on Thompson Avenue with Radio Recall.
- Saturday, Oct. 31, 9 a.m. to 1 p.m. The Town's Halloween Market at The Pavilion at Riverwalk Park, 1000 Chelsea Road.
- Saturday, Nov. 14, 7 p.m. Virginia's Li'l Ole Opry plays the second Arts Alive show.
- Saturday, Nov. 28, 9 a.m. to 1 p.m. The Holiday Market at West Point Town Park, 325 8th Street, on the same date the Chamber has set for Small Business Saturday.
- Sunday, Dec. 6. Christmas on the Town in the downtown waterfront district, with the parade at 1 p.m.
- Rest of December. Light Up the Point judging and the Chamber's trolley tours.
The two concerts set the pace for the first half. Arts Alive lists single tickets at $35 for adults and $15 for youth. A season subscription is $125, or $110 for seniors 65 and older, and covers four more shows running from February through May. Arts Alive is a nonprofit. Beyond the concerts, it runs workshops, camps, exhibitions, and scholarships.
Halloween at the Pavilion Introduces the Vendors
The Oct. 31 market is the season's only stop at Riverwalk Park. According to the Town's listing on Visit West Point & King William, vendors will sell seasonal produce, jewelry, gifts, baked goods, jams and jellies, autumn decor, and coffee. Kids get Gaga Ball, free face painting, and activities with the West Point Police Department, and lunch comes from Nino's Pizza Truck.
The jams and jellies, baked goods, and coffee matter because they come back four weeks later. The Town describes the Holiday Market as "our wonderful farmers market vendors, plus a few new additions." The Halloween Market works as a preview of who'll be selling wreaths and pies at Town Park on Nov. 28.
November 28 Has Two Things Going On
The Saturday after Thanksgiving is when the season moves to Town Park, and there's a lot happening that day. The Holiday Market's list includes fresh-cut greenery, centerpieces and wreaths, baked goods, jams and jellies, sweet treats, coffee, candles, artwork, dog treats, crafts, and health and wellness products. The Chamber has also set Nov. 28, 2026 as Small Business Saturday and says it plans an extra celebration with local business owners. The Chamber's shopping page still shows last year's deals, so this year's store promotions haven't been posted yet.
One store will be having its first holiday season. Holly Sowinski opened Wild Daisy Books at 2800 King William Avenue in January 2026. The Gazette-Journal reported ahead of time that the grand opening was set for Jan. 10. The shop sells mostly used books along with new titles and gifts, has a children's area, and offers free coffee and hot chocolate. The market runs from 9 a.m. to 1 p.m., so the afternoon is open for King William Avenue.
December 6, Hour by Hour
The Chamber calls Christmas on the Town the town's annual holiday kickoff. It's held on the first Sunday in December in the downtown waterfront district. The deadline for vendor applications was Oct. 11. These are the parts with posted times or locations:
| When | What | Where |
|---|---|---|
| 12:00 to 4:30 p.m. | Letters to Santa pickup and drop-off | Town Hall |
| 1:00 p.m. | Christmas on the Town Parade | Lines up on Kirby Street, then down Main Street |
| 2:30 to 4:30 p.m. | Pictures with Santa with Yours Truly Photography, no reservations | Town Hall |
| Time not yet posted | 5th Annual Chili Cook-Off and Christmas Cookie Contest, hosted by the West Point Volunteer Fire Department | 7th Street |
| Time not yet posted | Tree of Life Ceremony | Beach Park on First Street, with a second ceremony at King William Training School |
Anyone can be in the parade. There's no entry fee, you don't have to enter the float contest, and one entry wins the Best Holiday Spirit trophy. Dominion Energy sponsors the parade. Parents can take their own photos with Santa or use the photographer, who will have prints for sale. Letters to Santa can also be picked up and dropped off at Town Hall all through December, not only on parade day.
The Tree of Life Ceremony is the quietest part of the day. According to the Chamber's Christmas on the Town page, the Christmas tree at Beach Park is lit in honor of names that community members submit, whether family, friends, groups, or "those who we wish to never forget." The tree stays lit through the rest of the season.
Two of the Programs After the Parade Fund One Scholarship
The parade is the busiest afternoon. Three other Chamber programs keep going after it, and the trolley and the tree auction both raise money for the same thing.
Light Up the Point. Houses compete for Most Festive House in West Point. A panel judges them in December on theme and design, creativity, effort and participation, and overall look. Businesses are judged separately through an online community poll.
The trolley tour. The Chamber runs trolley rides past the decorated houses. Each tour holds 25 riders, you have to register in advance, and the Chamber asks for a $5 donation per rider. The 2026 tour dates aren't on the Chamber's page yet.
Festival of the Trees. Families, businesses, and organizations decorate a Christmas tree, wreath, or garland and donate it to the Chamber. Each piece goes into a silent auction.
The trolley donations and the auction bids both go to the Chamber's Workforce Development Scholarship. It goes to a West Point High School senior in spring 2027. Christmas on the Town itself is run by volunteers, who handle parade logistics, the information booth, and helping Santa with photos.
Eating Between Stops
None of the events above serves a sit-down meal, so lunch after the market or dinner after a concert means going downtown. The 3rd Annual West Point & King William Restaurant Week in March 2026 had 11 eateries. Their descriptions make a good starting list, though being in a March event doesn't confirm a place's December hours.
- The Pie Lady and Company serves breakfast, lunch, homemade pies and baked goods, sandwiches, and chicken salad.
- Tony & George's serves seafood and Italian food and is best known locally for its fried chicken.
- Lovell's Place serves home-style cooking with daily specials.
- Anna's Italian Restaurant & Pizza is a family-run place on King William Avenue serving pizza, pasta, baked entrees, subs, and calzones.
- The Blue Crab of WP focuses on steamed crabs, shrimp, and fish platters and has non-seafood options too.
- Roma Ristorante Italiano serves Italian comfort food, including seafood and shrimp pasta.
- Mattapony Reserve, at 1581 Mattaponi Reservation Circle, pours natural wines in a tasting room and museum and serves charcuterie and its signature Mattapony meat pies.
Restaurant Week returns in March 2027. Dates haven't been announced. The Town reports that construction on a 22,000-square-foot Tractor Supply at 3500 King William Avenue started Aug. 7, 2026, with completion forecast for March 2027. If the forecast holds, the new store will be one of the first new things on King William Avenue after this season ends.
If you're entering Light Up the Point this year and your ladder trip turns up a sagging gutter or a soft spot in the porch trim, I'm glad to take a look. I've built houses and sold them around here for close to thirty years, so I can tell you which fixes can wait until spring and which ones shouldn't. Get your instant home valuation or schedule a consultation with Berb at David Berberich.
