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A Seaside Christmas in Orleans

November 27, 2021 @ 9:00 am - 7:00 pm

The Orleans Chamber of Commerce kicks off its annual Seaside Christmas festivities with an array of holiday happenings on Saturday, Nov. 27th, including Breakfast with Mrs. Claus, the arrival of Santa, Winterfest Orleans events and amazing holiday deals during Small Business Saturday.

The day begins with sweet treats at the Breakfast with Mrs. Claus at the Orleans Yacht Club, 39 Cove Rd. This event is free, but donations will be accepted. In addition to delicious donuts and coffee from the Hole In One restaurant, Mrs. Claus will be on hand for photo opportunities as families wait for Santa, who arrives at 10 a.m. to meet and greet his fans and pose for pictures. We’ll be outdoors this year in heated tents.

Kids can follow Santa to Snow’s Home & Garden, 22 Main St., where he will listen to gift requests and take pictures with the little ones.

Then it’s on to holiday shopping during American Express’ Small Business Saturday, when shoppers can expect even more sales and specials from neighborhood shops and stores. Take a break from shopping to check out the new local band Rising Tide who will be performing from 1-2pm at the Old Firehouse Community Center, 44 Main St.

Festivities continue on Nov. 27th with the Orleans Improvement Association‘s Winterfest Orleans, including enhanced tree lighting on Main Street and the Candlelight Stroll down Main Street ending at Depot Square, where the big fir tree and a new sculpture will be lit. Winterfest Orleans is a collaboration with OIA, the Chamber of Commerce, and the Orleans Cultural District.

As if things weren’t exciting enough on Nov. 27, a holiday party hosted by the Artist Cottages at Orleans Marketplace, will be attended by Santa and Mrs. Claus and include live music, story time for kids, art by local artists and great giveaways!

On Saturday, Dec. 4th, all ages vie for trophies and prizes during the annual Santa Stampede 5K and Family Fun Run, which begins and ends at the Barley Neck Inn, 5 Beach Rd. A kids’ mile run starts at 10am and the Stampede at 10:30.  An after party and awards ceremony will take place outdoors in a heated tent for extra social distancing. See you there!

Through the month of December, check out the holiday decorations displayed by local businesses during the Holiday Decorating Contest. Vote for your favorites at participating locations and win tickets from Cape Air! The Decorating Contest is held in conjunction with the Orleans Improvement Association.



Join the Stampede. Sign up today!


November 27, 2021
9:00 am - 7:00 pm
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Orleans Yacht Club
39 Cove Rd.
Orleans, MA 02653 United States
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(508) 255-9091
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