Kittery's holiday calendar doesn't belong to any one organization. Kittery Trading Post starts it, a community market on Shapleigh Road carries it, and a pub and a dance hall on the Foreside take it over for Thanksgiving week. Then a service club, a community center and a crowd of parade entrants bring it across town to a single tree lighting. From Nov. 20 to Dec. 19 the season changes hands about once a week, and each host keeps to its own address.
The Week of Nov. 20 Starts at Kittery Trading Post
The first host is Kittery Trading Post. Its 18th Annual Food Round-Up is set for Nov. 20, 2026. Bring nonperishable food or personal-care items and you get a KTP gift card in return. The same day opens the store's Holiday Sale & Events, which runs through Nov. 29: 10 days of storewide savings plus free events. The store has posted the dates, and the event-by-event schedule is still to come.
The overlap is useful. The Round-Up sets the tone for the season as a collection drive before it becomes a shopping run, and the sale window covers both weekends that follow.
Nov. 22 to 24: From Post Office Square to Wallingford Square
Two days later the season moves to Post Office Square, 10 Shapleigh Road. Kittery Community Market holds its Outdoor Holiday Market on Sunday, Nov. 22, from 10 a.m. to 2 p.m. The market lists 35-plus vendors with local food, gifts, winter greenery and live music. It's the biggest vendor count of the season and the only market held outdoors, so it's the one to plan around if you buy your wreaths and greenery locally.
On Tuesday, Nov. 24, two days before Thanksgiving, the Foreside takes over. The Corner Pub at 4 Wallingford Square hosts its Winter Night Market from 5 to 9 p.m. It's the one evening market on the calendar, set on a weeknight when most holiday shopping in town has stopped for the day.
Thanksgiving Weekend Belongs to Walker Street
The Dance Hall at 7 Walker Street holds the long weekend. The Bang Group returns with Nut/Cracked on Saturday, Nov. 28, at 7 p.m. and Sunday, Nov. 29, at 2 p.m. The Dance Hall's listing describes it as The Nutcracker taken apart and rebuilt. Tchaikovsky's score is mixed with music by Duke Ellington and Glenn Miller, and the show includes tap, singing and some unusual pointe shoe work. The New York-based company, led by David Parker, first performed the piece at The Dance Hall in 2016.
Tickets are $30 in advance, $40 on the day and $20 for students, plus a $3 facility fee per ticket and card processing fees. The $10 gap between advance and day-of prices is a good reason to buy before Thanksgiving dinner takes over your week.
The Sunday matinee also means Walker Street hosts a family afternoon on the same weekend Kittery Trading Post's sale winds down on Nov. 29.
The Quieter Track Running on Rogers Road
Alongside the public events, the Kittery Community Center runs its own smaller calendar, with something for children and something for seniors. Some of these events require registration. Its special events page lists these dates:
- Letters to Santa, Nov. 27 to Dec. 11, with letters mailed to 120 Rogers Road, Kittery, ME 03904, or dropped in Santa's mailbox in the center's front lobby
- Gingerbread House Decorating, Dec. 1, 5 to 6 p.m., with no walk-ins and pre-registration due by Nov. 24
- Breakfast with Santa, Dec. 5, 8:30 to 10 a.m.
- Harbourside Garden Club Holiday Basket Workshop, Dec. 9, 1 p.m., a free workshop for up to 50 seniors ages 55 and up, with advance registration required
Letters to Santa opens the day after Thanksgiving and closes the week after the parade, which makes it the longest-running item on the town's holiday calendar. Breakfast with Santa is where this quieter track joins the main event.
Dec. 5: The Day the Hosts Converge
Saturday, Dec. 5, is the one day when several of these hosts share the calendar. The morning starts on Rogers Road, and the afternoon belongs to the Kittery Holiday Parade, sponsored again this year by the Kiwanis Club of the Seacoast.
- 8:30 to 10 a.m. Breakfast with Santa at the Kittery Community Center.
- 3 p.m. The parade steps off from Traip Academy.
- At the finish The parade ends at John Paul Jones Park with the tree lighting.
The 2026 theme is "Holiday Traditions Through The Decades." Businesses, youth groups, individuals, families and community organizations are all invited to enter a float or marching group. Kiwanis lists safety rules for vehicle and float entries. Float trailers need wheel fenders, and children riding outside the driver's compartment need an adult other than the driver supervising them. For questions about entering, the club takes email at [email protected].
The open entry list is what turns the parade into the handoff. It's the one event on the calendar where any household, team or shop can be part of the show.
Dec. 6: The Market Comes Back Indoors
The next morning the season returns to 10 Shapleigh Road, this time indoors. Kittery Community Market's Annual Holiday Sip & Shop runs Sunday, Dec. 6, from 10 a.m. to 2 p.m. inside Blue Mermaid and Tributary Brewing Co. Twenty-five of the market's local artisans sell handmade gifts alongside brunch and beer.
On Nov. 22, the outdoor market had 35-plus vendors and greenery in the open air. Two weeks later it's a smaller, handmade-focused group under one roof, with food and drink as part of the draw. Same organizer, same address and same four-hour window, but a different market.
The Season at a Glance
| Date | Event | Host | Where |
|---|---|---|---|
| Nov. 20 | Food Round-Up; Holiday Sale begins | Kittery Trading Post | Kittery Trading Post |
| Nov. 22 | Outdoor Holiday Market, 10 a.m. to 2 p.m. | Kittery Community Market | Post Office Square, 10 Shapleigh Road |
| Nov. 24 | Winter Night Market, 5 to 9 p.m. | The Corner Pub | 4 Wallingford Square |
| Nov. 28 and 29 | Nut/Cracked | The Dance Hall | 7 Walker Street |
| Dec. 1 | Gingerbread House Decorating | Kittery Community Center | Community Center |
| Dec. 5 | Breakfast with Santa; Holiday Parade and tree lighting | Community Center; Kiwanis Club of the Seacoast | Traip Academy to John Paul Jones Park |
| Dec. 6 | Holiday Sip & Shop, 10 a.m. to 2 p.m. | Kittery Community Market | Blue Mermaid and Tributary Brewing Co. |
| Dec. 9 | Holiday Basket Workshop | Harbourside Garden Club | Community Center |
| Dec. 12 | Christmasland Jubilee | The Dance Hall | 7 Walker Street |
| Dec. 19 | Home for the Holidays | The Dance Hall | 7 Walker Street |
After the Tree Is Lit, Walker Street Closes It Out
When the parade and markets are over, the last two hosts on the calendar are both at The Dance Hall. Dan Blakeslee's Christmasland Jubilee plays Saturday, Dec. 12, from 7:30 to 9 p.m. One week later, Jason Anderson + Friends: Home for the Holidays runs Saturday, Dec. 19, at the same time, with proceeds going to Cross Roads House.
That makes Walker Street the bookend of the season. It hosts the Thanksgiving weekend shows and the final two Saturdays before Christmas, and the Foreside around it has more to offer this year than last. Kittery Wine Bar opened on the same street at 10 Walker St. as an independently owned wine bar and retail shop, Mainebiz reported in July. The Foreside Inn is now open at 29 Wentworth St., with 24 guest rooms in two buildings, according to Seacoastonline on Oct. 21. That gives visiting family a place to stay on the Foreside during the December shows.
One more addition is on the way. Perkins Cove's Foot Bridge Lobster plans a year-round Kittery location, the Portsmouth Herald reported on Oct. 14. The paper framed it as an answer to winter lobster roll cravings that until now had to wait for tourist season to return.
If the season has you thinking about where your own Kittery home stands as the year ends, Great Seacoast Homes would be glad to help. Request a Personalized Home Valuation, and we'll talk it through in time for the new year.
