The top three homes in this year's Trick Out Orleans contest won't get a pumpkin trophy or a gift card. Each one gets a holiday wreath from The Farm in December. The three winning storefronts get December holiday décor that The Farm designs and installs. Every business that entered gets a holiday decoration to put up in December, win or lose. The Town of Orleans set up its October contest to pay out after Thanksgiving. That choice says a lot about how the town plans the ten weeks ahead. Halloween and the holidays are now planned as one public season, with Main Street and the Village Green carrying it from start to finish.
The prize list explains the plan
Trick Out Orleans had two registration windows, one for residents and one for businesses, and both closed October 12. Registered homes show up on a live map of decorated houses across town, and the public votes online for the winners. Storefronts had the same setup, with pumpkins, cornstalks, scarecrows, or any spooky idea a shop owner wanted to try. Details are on the Town's September 2026 Town Talk.
The Farm is a locally owned, family-run nursery and garden center, "Rooted at Rock Harbor Road." The Farm isn't new to the Town's holiday plans. Last December, the Town thanked it for the wreaths on Town Hall, the DPW, the Police Station and the Fire-Rescue Station. This year, the same nursery's work will also show up on whichever houses and shops the public votes into the top three.
Questions about the contest go to Jamie Demetri, whose title, Recreation, Culture & Community Events, describes the job well. Orleans already had that role by August 2025, when the Cape Cod Chronicle reported that the town's recreation programming had grown in recent years.
This Saturday shows how the parts fit together
The OES Parent-Teacher Halloween Stroll runs Saturday, October 24, from 3:00 to 4:30 p.m. The parent-teacher group runs the stroll, and the Town helped businesses sign up as official candy stops. Each registered stop got a free 2-pound bag of candy and a spot on the live Stroll map. On October 31, a second live map shows the homes that registered as trick-or-treat stops.
October 24 is busy for other reasons, too. It's the deadline to register to vote in the November 3 state election. It's also the one Saturday of early voting with full hours, 9 a.m. to 5 p.m. at Town Hall, 19 School Road. If you're heading to School Road that afternoon, give yourself extra time.
Last December, the Village Green was the first step
Buoys of Joy went up on the Village Green last December. It is three illuminated buoy sculptures that spell J-O-Y, built from reclaimed marine materials. Orleans artist Scott Feen of Atlantic Workshop created it with artists Elaine and Beatrice Alder, artisan Tiran Dagan, and student volunteers from Nauset Regional Middle School. The sculptures have aluminum frames wrapped in repurposed aquaculture mesh, fishing nets and lobster bait bags. The students made the red and green letters from reclaimed clam-bag netting. The Orleans Cultural Council and CARE for the Cape & Islands helped pay for it.
The Town's December 2025 Town Talk called Buoys of Joy part of "a broader holiday placemaking effort." The Town said the effort aims to improve key public spaces, support local artists, and offer "a distinctive alternative to traditional holiday décor." It called the Village Green "the first location." The Cape Cod Chronicle covered the installation at the end of last season. The Town hasn't said yet where the buoys or a second installation will go in 2026. Still, "first location" points to more than one, and the December prizes from this fall's contest will add to the same effort along Main Street.
The November and December calendar
Several groups run separate pieces of the season, and some of them have already posted 2026 dates. Here they are in order:
- Santa Arrives by Boat, Saturday, November 28, 8:15 to 8:30 a.m. The Harbormaster's boat brings him to Town Cove Dock at 39 Cove Road, according to the Orleans Chamber of Commerce listing.
- Breakfast with Santa & Mrs. Claus, the same morning. The Chamber lists it for November 28. Last year's breakfast had an 8 a.m. seating at Orleans Yacht Club, where guests could watch Santa's boat come in from the patio. The Cape Cod Chronicle reported that staff from The Rail and Barley Neck served the 2025 meal.
- Nauset Model Railroad Club Holiday Open House, Saturdays from November 28 to December 26, 1 to 4 p.m. Admission is free.
- First Friday Holiday Edition, Friday, December 4. The First Friday site lists 3 to 7 p.m. The Chamber's listing says 5 to 8 p.m. Check the official page closer to the date.
- Santa Stampede 2026, Saturday, December 5, at The Barley Neck.
- Solstice Sparkle, date in December still to be set. The Orleans Cultural District describes a two-day event. Last year it ran December 20 and 21, with a Solstice Storytime and Gentle Yoga at Snow Library and a Solstice Labyrinth Path on the Village Green.
The Chamber's Thanksgiving-weekend schedule from last year gives a good idea of what to expect, though none of it is confirmed for 2026. In 2025, a town trolley ran from 4 to 8 p.m. on Friday. Candlelit caroling went from Snow Library to Depot Square at 4:30. The Orleans Improvement Association lit the tree at 5:30, and downtown shops stayed open until 8. On Saturday, horse-and-carriage rides left from 44 Main Street between 1 and 4 p.m.
Who runs what
Several groups share the season, and the Town's pieces are the ones that run from October into December.
| Organizer | What it runs | 2026 status |
|---|---|---|
| Town of Orleans, Recreation, Culture & Community Events | Trick Out Orleans contest and maps, stroll candy-stop registration | Underway |
| OES Parent-Teacher group | Halloween Stroll | October 24, 3 to 4:30 p.m. |
| The Farm | Contest prizes, delivered in December | Winners decided by public vote |
| Orleans Chamber of Commerce | Santa by boat, Breakfast with Santa | November 28 |
| Chamber, Town and Orleans Merchants Group | First Friday Holiday Edition | December 4 |
| Orleans Cultural District | Solstice Sparkle | December, date to be set |
| Town placemaking effort | Buoys of Joy, Village Green | 2026 plans not yet announced |
First Friday shows the same pattern on a smaller scale. It started in 2024 as a Chamber project. It's now run jointly by the Chamber, the Town and the Orleans Merchants Group, which share promotion, planning and logistics. The 2026 schedule had editions in June, July, August and September, skipped October and November, and returns for December. In September, participants included Sea Howl Bookshop, Main Street Wine & Gourmet, The Sparrow Store at 26 Main Street, and The Rail and Barley Neck in East Orleans. The December list of participating businesses hasn't been posted yet.
Eldredge Park is closed this winter
Eldredge Park, the town's other big public space, is out of use this year, which leaves Main Street and the Village Green to carry the season. All of the park's facilities, including the courts and playground, have been closed since September 9 for renovation. The contract covers six pickleball courts, two tennis courts, a basketball court and a playground. It also includes alternates for an extra court area and for pedestrian and court lighting. The target for substantial completion is May 21, 2027, with final completion by June 10, 2027. The Cape Cod Chronicle reported in April that the Town had asked for $5 million in Community Preservation Act funds and voters approved $3 million, on top of $850,000 in free cash approved earlier.
Until the park reopens, the Town points players to the tennis and pickleball courts at Orleans Elementary School. They're open Monday, Wednesday and Friday after 5 p.m., Tuesday and Thursday after 4:30, Saturday after noon, and all day Sunday. The OES playground is open weekdays after 2:30 p.m. and all day on weekends. Finlay Road is also closed to through traffic in both directions while crews install a new sewer force main at Route 28. Detours run through Eldredge Park Way, so expect more traffic near the park through the winter. The Eldredge Park project page posts milestones and photos as work moves along.
If you're putting together a December in Orleans this year, with family coming for Santa's 8:15 boat or a seasonal home that needs opening up, getting through the winter, or getting ready for spring, the team at Guthrie Schofield Group knows these Lower Cape weeks well and is happy to help you plan. Get in Touch.
