View All 5th Annual Holiday Stroll Photos Here!

Special thanks to Dave Robbins Photography for beautifully capturing the spirit of the Holiday Stroll and generously sharing these photos with our community.

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.

 
View All Promotions
Holiday Stroll Event Map
 

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.

 

Thank You to Our Sponsors

 
 

2025 Participating Vendors

 
 

Participating Westport Businesses

 

The Animal Muse | Home-based in Westport — Animal Communication + Reiki Holiday Bundle. Save $50

American Colors by Henry Lehr I 66 Post Rd East — 20% off Hampton wash and American Colors cloth (During Holiday Stroll 4-7 pm)

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

Bloom Salon | 14 Elm St. Suite 205 — Holiday Treats and Discounted Hair Tinsels (During Holiday Stroll 4-7 pm)

Bridgewater Chocolate | 165 Main Street — For any customer who makes a purchase during the stroll, they will be entered into a drawing to win a $50 gift card (During Holiday Stroll 4-7 pm)

Brooks Brothers | 136 Main Street — 30% off almost everything, plus a special invitation if you walk in during the stroll hours (During Holiday Stroll 4-7 pm)

Candle Caboodle | Home-based in Westport — TBA (During Holiday Stroll 4-7 pm)

Chait Gallery/ Photography Studio | 11 Riverside Avenue, 2nd Floor — 30% Off all Artwork / Artistic Photographic; Portraits in Studio $200 for 1 1-hour session includes 1 8x10 print (During Holiday Stroll 4-7 pm)

Chocolatieree I 66 Church Lane — Blissfully toasted & gooey S'morestick with every purchase (min $20) (All Day 12/6)

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 holiday songs with live music from Warren Bloom (5 -7 pm)

Core Burn Pilates Westport | 12 Elm Street — Discounted group class and private sessions available for purchase during the stroll! (During Holiday Stroll 4-7 pm)

Courtgirl | 125 Main Street, 3rd Floor — 15-30% off store wide (All Day 12/6)

Cold Fusion Gelato | 178 Main Street — Free wrapped chocolates (During Holiday Stroll 4-7 pm)

Earthplace | 10 Woodside Lane — 10% off Earthplace's Winter Solstice Campfire on Sunday, December 21st. The discount will be applied to all Campfire registrations placed on December 6th. (All Day 12/6)

Eleish Van Breems | 177 Main Street — Cider in the courtyard and running a raffle for a Tomte (All Day 12/6)

Everything But Water I 136 Main Street — $25 off $150+ with Beach Club signing; Fit sessions (All Day 12/6)

Faherty | 26 Main Street — Refreshments and Good Vibes! (During Holiday Stroll 4-7 pm)

fred | 30 Post Road East — Gift with purchase (All Day 12/6)

Gabriele’s of Westport | 27 Powers Court — Buy $500 worth of gift cards and receive $100 extra on us (Valid now through 12/25/25)

Gioiella Jewelry | 1 Greystone Farm Lane — Raffle (During Holiday Stroll 4-7 pm)

Hummingbird Healing Center | 57 Main Street, 2nd Floor — Light bites, wine, Harmonic Egg® Raffle (During Holiday Stroll 4-7 pm)

Il Pastaficio | 135 Post Road East — Focaccia di Recco, Italian Hot Chocolate, Salame di Cioccolata, and a gift card for a 10% off purchases of Fresh pasta boxes and sauces. (12/6 from 11:00 am to 5:30 pm)

J. McLaughlin | 382 Post Road East — 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!

Joe's Pizza | 190 Main Street — Garlic Knots (During Holiday Stroll 4-7 pm)

Johnny Was I 81 Main Street — 40% Off Sale, Complimentary gift wrapping event & Gift with purchase (All Day 12/6)

Just Salad | 275 Post Rd East — 10% OFF* online or on the Just Salad app with code STROLL10. *Excludes in-store purchases. (Valid until 12/31/2025)

Kerri Rosenthal | 181 Main Street — 20% off excludes Winter 25, Original Art, and Third Party (During Holiday Stroll 4-7 pm)

LaSource | 7 Church Lane — Every purchase of $100 or more will be entered to win a $500 LaSource Gift Card (During Holiday Stroll 4-7 pm)

lululemon | 69 Main Street — Complimentary hot chocolate from Oggi Gelato, and a chance to win a curated basket—packed with lululemon favorites and an Oggi Gelato gift card! One free entry for every $200 spent! (During Holiday Stroll 4-7 pm)

Lux Bond & Green | 136 Main Street — A glass of holiday cheer and treats (During Holiday Stroll 4-7 pm)

Massi Co | 90 Post Rd East — Hot Cider (During Holiday Stroll 4-7 pm)

Naturino Kids Shoes & More Westport | 1096 Post Rd East —25% OFF a single pair *Excluding Sorel & Kane (All Day 12/6)

Nomade | 150 Main Street — Free smore's and free Advent Calendar in front of Nomade (During Holiday Stroll 4-7 pm)

Offline by Aerie | 91 Main Street — 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)

Paper Source | 100 Post Road East — BOGO 50% off Holiday Boxed Cards / PWP Selected Holiday Deco / Instant 10% Discount for Premium Member (All Day 12/6)

Rhone Westport | 7 Main Street — Complementary beverages and 15% off first purchase (During Holiday Stroll 4-7 pm)

Rowan | 47 Main Street — Buy 2 non-piercing pairs of earrings, get the 2nd at 15% off (All Day 12/6)

Salon Nash I Mobile, Based in Westport — Glow + Go Facial + Blowout Special for $200; call Felicia at 203-747-9753 (Valid until 12/31)

Savvy + Grace | 146 Main Street — North Pole Mailbox for letters to Santa (During Holiday Stroll 4-7 pm)

Scout & Molly’s | 283 Post Rd East - Free gift with $200 purchase (During Holiday Stroll 4-7 pm)

SHOE-INN | 21 Main Street — Winter Sale, up to 75% Off! (All Day 12/6)

Sorelle Gallery | 19 Church Lane — 20% off original artwork and prints all day, plus champagne and holiday treats (All Day 12/6)

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

Splash of Pink | 275 Post Road East —Free gift with purchase over $200 (All Day 12/6)

Sweet P Bakery | Online — $5 Off Colossal Cookie Box + Free Shipping (12/31)

SWTHZ | 374 Post Road East, Suite 80 — $10 off a 60-minute Contrast Therapy session in their Private Luxury Suites with code STROLL (Valid through 12/31/25)

Theory | 87 Main Street — Holiday Sip and Shop (During Holiday Stroll 4-7 pm)

The Toy Post | 180 Post Road East — Small gifts to children of all ages (During Holiday Stroll 4-7 pm)

Vince Westport | 115 Main Street — 25% off (All Day 12/6)

W Hair & Color | 1391 Post Rd East — A raffle for a package of 3 blowouts (During Holiday Stroll 4-7 pm)

Walrus Alley | 90 Post Road East — Happy Hour featuring our famous Glühwein (During Holiday Stroll 4-7 pm)

West Elm | 35 Main Street — General company promotions across our collections.

Westport Centerpiece | Home-based in Westport — Holiday gifts (All Day 12/6)

Westport Book Shop | 23 Jesup Road — Stop by the Westport Book Shop on your way to the Holiday Stroll! Gift with purchase of children's books to kick off the festive season! (During Holiday Stroll 4-7 pm)

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 enjoy exclusive discounts. Purchase your tickets for our upcoming Holiday season shows. (All Day 12/6)

West Out East | 1 Main Street — 15% off all accessories (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)