Where does Port Washington's holiday season actually happen? The Greater Port Washington Business Improvement District's answer is "townwide." That's true of the deals and the window displays. But look at the 2026 calendar date by date and one address keeps coming up. Landmark on Main Street co-presents Port Holiday Magic. Its theater hosts the Thanksgiving weekend Nutcracker. Its gym is the indoor base for Giving Saturday. In the week after that, its stage has a holiday show on four of the next five nights.
So for anyone who lives here, the season comes down to a question of timing around one building.
Three jobs under one roof
The Port Holiday Magic page names three presenters: the Port Washington Chamber of Commerce, Landmark on Main Street and Residents Forward. The Dejana Family Foundation and the Greater Port Washington BID are listed as supporters, and the Town of North Hempstead, the local police and fire departments help out.
Landmark does three different things across the season:
- Co-presenter of both Port Holiday Magic Saturdays, on Nov. 28 and Dec. 5
- Theater for the Nutcracker over Thanksgiving weekend and four holiday concerts from Dec. 6 to Dec. 10
- Gym for Santa photos and Santa's Magical Village on Dec. 5
Each job puts the building on a different day, so the sections below go through the season in order.
Nov. 28: the street and the stage share an afternoon
The first Port Holiday Magic Saturday is Small Business Saturday, two days after Thanksgiving. Santa starts things off at 12 noon on a firetruck, riding from Port Washington Boulevard to Manorhaven Boulevard. From 11 a.m. to 3 p.m., "Shoppertainment" brings live performances, costumed characters and singing toy soldiers to participating businesses on Main Street. A free hop-on, hop-off trolley with live music runs during the same hours.
Participating stores offer deals, discounts and holiday refreshments all day. Look for red bows on the storefronts. The BID points people to its Try Port First app for the list of participating stores, their offers and the trolley stops.
While all that is happening outside, Long Island Ballet Theater is putting on The Nutcracker inside Landmark at 1 p.m. and 4 p.m. The run continues Sunday, Nov. 29, at noon and 3 p.m.
Because the 4 p.m. show starts an hour after the trolley stops running, a family can fit the whole Saturday on one street:
- Get to Main Street by 11 a.m., when the trolley and Shoppertainment start.
- Catch Santa's firetruck run at noon.
- Spend the early afternoon at the stores with red bows.
- Walk into Landmark for the 4 p.m. Nutcracker after the street events end at 3.
The production is narrated and slightly shortened. It runs 90 minutes plus an intermission and is billed as suitable for children as young as 3. After each show, children ages 3 to 10 can go on stage for a reception called Kingdom of the Sweets to meet the cast, take pictures and get a goody bag. The cast includes professional dancers from Ballet Hispanico and Chavalier Ballet alongside student dancers from across Long Island.
The production is an independent artist booking at Landmark, so Landmark's box office doesn't sell tickets to it. Tickets are sold through the ticket link on Landmark's event page. Prices are $40 for adults and $25 for children ages 3 to 12.
Dec. 5: Giving Saturday moves into the gym
On Nov. 28 the action is out on the street. The second Saturday moves indoors. The BID calls Dec. 5 Port Washington's own "Giving Saturday," and its slogan for the day is "Buy Local to Give Local."
Both main events are at Landmark Gym on Main Street:
- 11 a.m. to 2 p.m. Santa's Magical Village, with refreshments, live music and a meet-and-greet with local nonprofit organizations
- 12 to 2 p.m. Free photos with Santa and live performances
The BID describes the day as bringing local nonprofits "under one roof to make giving easy." Participating businesses around town also serve as collection sites for the Make a Child Smile toy drive. Last year, Long Island Press reported that the Chamber's 2025 drive collected new, unwrapped toys, nonperishable food and diapers for local children and families. For this year's collection sites, check the Try Port First app.
The storefront window decorating contest runs all week, and final awards for best painted and best decorated windows will be announced. In 2025, according to Long Island Press, Beacon Pharmacy won Best Painted, Lifestyle Café won Most Creatively Decorated and S.F. Falconer Florist won Most Beautifully Decorated. Those windows set the bar for this year's entries.
Dec. 6 to 10: the stage takes over
Giving Saturday ends at 2 p.m., and Landmark's theater starts the next night. From Dec. 6 to Dec. 10, the building that hosted Santa and the nonprofits has a holiday show on four nights:
| Date | Show | Time |
|---|---|---|
| Sunday, Dec. 6 | Darlene Love, "Love For the Holidays" | 7 p.m. |
| Monday, Dec. 7 | Christmas with Chris Ruggiero | 7 p.m. |
| Wednesday, Dec. 9 | Festival of Music and Light | 7 p.m. |
| Thursday, Dec. 10 | Big Bad Voodoo Daddy, "Wild & Swingin' Holiday Party" | 7:30 p.m. |
The Wednesday show is the most local of the four. The Festival of Music and Light is a free Chanukah concert, with registration through Landmark, for "the entire Port Washington community." Four congregations present it together: Temple Beth Israel, Reconstructionist Synagogue of the North Shore, Community Synagogue and Port Jewish Center. Chanukah 2026 runs Dec. 4 through 12, so the concert falls in the middle of the holiday.
Count from the morning of Dec. 5 to the night of Dec. 10 and that one address has holiday programming on five of six days. The Dec. 9 concert is free, and Landmark's event page has a registration link for it.
Beyond Main Street
Two other venues frame the Landmark-centered season, one before it starts and one after it ends.
The Port Washington Public Library starts things off. The Island Hills Chorus performs "Jingle All the Way," an a cappella program of holiday songs, on Sunday, Nov. 22, from 3 to 4:30 p.m., six days before Small Business Saturday. The library comes back on Friday, Dec. 11, from 7 to 8:30 p.m., with the Port Washington Play Troupe's "A Christmas Carol – A Radio Play."
Sands Point Preserve takes over the following weekend. Holiday Tales runs Saturday, Dec. 12, from 1 to 4 p.m. at Hempstead House, with Santa and Mrs. Claus, seasonal crafts, a dreidel corner, puppet shows and holiday music. The Preserve's Enchanted Holiday Adventure on Sunday, Dec. 20, also at Hempstead House, has two limited-capacity sessions, from noon to 1 p.m. and from 12:30 to 1:30 p.m.
Put in order, the season looks like this:
- Nov. 22: library chorus
- Nov. 28 and 29: Small Business Saturday on Main Street and the Nutcracker at Landmark
- Dec. 5: Giving Saturday in Landmark Gym
- Dec. 6 to 10: four holiday shows on Landmark's stage
- Dec. 11: the Play Troupe at the library
- Dec. 12 and 20: Hempstead House at Sands Point Preserve
Landmark accounts for the busiest stretch, from Thanksgiving weekend to Dec. 10. The library and the Preserve cover the weekends before and after it.
At Team Knoell, we keep track of North Shore calendars like this one because they show how a town actually spends its weekends, and how close a home is to Main Street matters most in a month like December. If you're curious what your Port Washington home is worth this season, start with our Get Your Instant Home Valuation tool and then talk it through with our family.
