The Orleans Chamber of Commerce kicks off its annual Seaside Christmas festivities with an array of holiday happenings on Friday November 28th, including Breakfast with Mrs. Claus, the arrival of Santa, Winterfest Orleans events and amazing holiday deals during Small Business Saturday. Bring the family to this wonderful Cape Cod weekend event to kick off the Christmas Holiday season.
See all 2025 Cape cod Christmas Holiday events
ORLEANS CHAMBER OF COMMERCE PRESENTS
‘TIS THE SEASON
Small Business Weekend Stroll | November 28th & 29th
- The start of the most important season for our small businesses
- Orleans open late (check store listings)
- Shopping | Art Galleries | Live Music | Dining | Pop Ups
Annual OIA Tree Lighting | Friday November 28th
- 4:30 Stroll begins from Library | 5:15 pm Gather at Depot Square
- 5:30 pm Tree Lighting
Breakfast with Santa & Mrs. Claus | Saturday November 29th
- Brought to you by Cape Cod 5 | Breakfast by The Rail
- Reservations required for Breakfast at Orleans Yacht Club
- Santa arrives at 8:15 am to Cove Road Town Landing escorted by Orleans Harbormaster Team
Main Street Horse & Carriage Rides | Saturday November 29th
- Horse & Carriage Rides 1 pm – 4 pm begin/end in front of 44 Main Street
Santa Stampede | December 6th
- Brought to you by Friends’ Marketplace
- 8:30 am Registration Table opens
- 9:30 am FREE Fun Run for kids
- 10:00 am 5K STARTS
- 11:00 am After Party – Included in Runner Registration
- Not Running? – Purchase After Party Ticket for $15
- 12:00 pm Awards
East Orleans Holiday Hop | December 6th
- Come explore the East Orleans Holiday Market | Village Wide