We are co-sponsoring the fifth annual Holiday Stroll with Dan Woog’s "06880." This year's event will feature participating retailers and restaurants offering deals and promotions, activities for children (face painting, s’mores, Santa photos, and more), and performances by the Staples High School Orphenians on Upper Main Street, Lower Main Street, corner of Post and Main outside Anthropologie, and Sconset Square. The Elm & Main complex at 136 Main Street will serve as the headquarters of Holiday Stroll with Santa, a DJ, a photo booth, and much more.

The Holiday Winter Market in the Elm & Main Lot will feature food vendors, holiday shopping, activities for the whole family and more! (See participating vendors below) The Westport Police Department will host a toy drive, so please bring a new toy.

Holiday Stroll Details for Westport Businesses

Holiday Stroll Promotion Submission Form
 

We invite all Westport based merchants, including retailers, restaurants, and service businesses, to participate.

Please share details about your planned specials or promotions by completing this form no later than Wednesday, December 3, at 3:00 PM to ensure inclusion on our website and in digital promotions.

 
 
View All Promotions (TBA)
 
Event Map (Coming Soon)
 

2025 Participating Vendors

TBA

Participating Westport Businesses

Bella Bridesmaids | 19 Post Road W - $25 off per dress! (All Day 12/6)

Bloom Salon | 14 Elm St. Suite 205 - Holiday Treats and Discounted Hair Tinsels (During Holiday Stroll 4-6 pm)

Candle Caboodle | Home-based in Westport - TBA (During Holiday Stroll 4-6 pm)

Clarendon Fine Art | 22 Main Street - Share a bit of holiday cheer as you browse great gifts for the art lovers in your life. Enjoy your favorite holidays songs with live music from Warren Bloom (5 - 7pm)

J. McLaughlin | 382 Post Road E - Drawing to all who stop in to browse or shop between 10 am and 6:00 pm and fill out a raffle slip to win one of our beautiful handbags! We will have holiday cookies and prosecco available in the afternoon!

Kerri Rosenthal | 181 Main Street - 20% off excludes Winter 25, Original Art, and Third Party (During Holiday Stroll 4-6 pm)

Lux Bond & Green | 136 Main Street - A glass of holiday cheer and treats (During Holiday Stroll 4-6 pm)

Nomade | 150 Main Street - Free smore's and free Advent Calendar in the front of Nomade (During Holiday Stroll 4-6 pm)

Offline by Aerie | 91 Main St - 10% off your purchase, plus 25% off of $125 if you book an appointment, as well as TBD in store promos (All Day 12/6)

Savvy + Grace | 146 Main Street - North Pole Mailbox for letters to Santa (During Holiday Stroll 4-6 pm)

Southern Tide | 33 Elm Street, Unit 1A - $50 off $150 or more (All Day 12/6)

Theory | 87 Main Street - Holiday Sip and Shop (During Holiday Stroll 4-6 pm)

The Toy Post | 180 Post Road E - Small gifts to children of all ages (During Holiday Stroll 4-6 pm)

Walrus Alley | 90 Post Road East - Happy Hour featuring our famous Glühwein (During Holiday Stroll 4-6 pm)

West Elm | 35 Main St - General company promotions across our collections.

Westportcenterpiece | Home-based in Westport - holiday gifts (All Day 12/6)

Westport Country Playhouse | 25 Powers Court - Get ready for the festive season with our exclusive offers! Enter our Raffle Gift Giveaway — win prizes and special surprises and njoy exclusive discounts. Purchase your tickets for our upcoming Holiday season shows. (All Day 12/6)

Zoomin Groomin | Mobile, Based in Westport - $25 off any mobile grooming services booked on the day of the stroll (for a future date) (All Day 12/6)