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 on Elm Street (Sigrid Schultz parking lot) will feature a variety of vendors for your shopping pleasure. (See participating vendors below). The Westport Police Department will host a toy drive, so please bring a new toy.

Thank You to Our Sponsors

2024 Participating Vendors in the Holiday Winter Market

Alina’s Cakes & Cookies, 1252 Post Road East — Complimentary hot chocolate

bartaco, 20 Wilton Rd — Samplings of bartaco’s finest!

Bloom Salon, 14 Elm Street, Unit 205 (new location opening 12/10/24) — Visit Bloom Salon’s vendor booth to purchase holiday gift sets and gift cards. Stop by the salon for complimentary hair tinsel, 10% off vouchers on a future service, and holiday refreshments on 12/7 during stroll hours between 5-7 pm.

BrandNu Apparel — Athletic wear

Candle Caboodle — Buy one candle and get a mini dessert candle for free! Valid while supplies last during stroll hours between 5-7 pm

Cove Collective, 26 Railroad Place — 15% off and festive treat all day on 12/7

CY Collective — Fashionable jewelry for all occasions

Haven Hot Chicken, 596 Westport Ave, Norwalk — Fried chicken samplers

Homes with Hope, 59 Myrtle Ave — Complimentary hot chocolate

Hughie’s Jewelry, 3449 Post Road, Southport — Specializing in buying and selling fine estate jewelry, gold, coins, and more! 

Huntington Learning Center, 272 Post Rd East — Stop by their booth to enter to win an amazing Holiday Basket filled with goodies to brighten up your season! They are also offering $100 off your academic evaluation—perfect for setting educational goals for the New Year.

LEVENthal Bakery — Free cookie samples & raffle ticket with purchase (to win a custom cookie) on 12/7 during stroll hours between 5-7 pm

Renewal by Andersen, 425 Post Rd E — Windows for cold weather

Singular CT — Designer shoes, handbags, and leather goods

Squeeze Massage, 625 Post Road East — 25% off gift cards, treat your loved ones with self-care for the holidays! Valid through 1/2/25 with Code: GIFT25

Sweet Bond — Permanent jewelry

The Clubhouse Westport, 1620 Post Rd East — Opening Jan 2025! Pick up holiday gifts like merch and gift cards, participate in a putting competition, and enter a giveaway to win The Ultimate Clubhouse Experience!

Waxing The City, 275 Post Rd East — Body waxing promotions

Westport Country Playhouse, 25 Powers Court — Use code STROLL25 for a 25% discount for up and running 2 play packages from 12/7 at 5 pm through the end of the day Sunday, 12/8

Westport is the Bestport — Westport logo wear makes the perfect holiday gifts

Participating Westport Businesses

Advanced Dog Behavior Solutions, 132 Compo Rd South — $150 off enrollment in the Puppy Primer dog training program when you mention the Holiday Stroll through 12/20

Animal Muse Communication and Reiki, 27 Oakview Circle - Complimentary Animal Reiki session with a VIP Animal Communication Session (mention Holiday Stroll) all day on 12/7

AROGYA Holistic Healing & Tea, 131 Post Rd East — Complementary Hot Tea to go on 12/7 during stroll hours between 5-7 pm

Arezzo Ristorante, 5 Riverside Avenue — One complimentary wine glass per person and half-priced appetizers on 12/7 during stroll hours 5-7 pm

Basso Restaurant and Wine Bar, 33 Jesup Rd — Complimentary House Cocktail, or Sangria with the purchase of an entree on 12/7 during dinner service from 5 PM until closing

Bella Bridesmaids, 19 Post Rd West — $50 off $500 or more all day on 12/7

Bobbles & Lace, 11 Church Lane — Wine and bobbles bucks ($10 off a future purchase) all day on 12/7

Bridgewater Chocolate, 165 Main Street - Anyone who makes a purchase during the stroll will be entered into a raffle where they can win a $50 gift card on 12/7 during stroll hours 5-7 pm

Castle Wine & Spirits, 1439 Post Rd East — Free Castle Wine 6-bottle tote bag with purchase all day on 12/7. When a tote bag is used for future purchases of applicable wines, get 5% off.

Catherine H., 144 Main Street — The holiday stroll is the kickoff to their exclusive holiday drawing: Every purchase this holiday season gives you an entry to win! Drawing will take place on 12/24

Chait Photography Gallery, 11 Riverside Ave. 2nd Fl — 30% off fine art photographic prints and $100 off Portrait Photography on 12/7 during the stroll from 4-7 pm

Chocolatieree, 66 Church Lane — Receive one raffle entry with every in-store purchase for a chance to win a holiday bundle: a mug, hot cocoa pack, and a 'Letter to Santa' kit. All day on 12/7

Clarendon Fine Art, 22 Main Street — Join Clarendon for a toast of holiday cheer! Collectors will receive a complimentary coffee table book of artwork with purchase, valid through 12/24

Cobs Bread, 374 Post Rd East — Buy any 6 scones, get a free Cranberry & Sea Salt French Baguette (in-store only) from 12/7 - 12/11

Cold Fusion Gelato, 178 Main Street — Free wrapped chocolates on 12/7 during stroll hours 5-7 pm

Core Burn Pilates, 12 Elm Street — One free 30-minute private session or one free group class plus 10% off any regular-priced package. Sign up during the stroll, and receive a free pair of Core Burn Pilates grip socks all day on 12/7

Crafty Kids Westport, 1019 Post Rd East — Arts & Crafts Station on 12/7 during stroll hours 5-7 pm

Diana Blau Author, 12 Center Street — Children's picture book sale “Beary & Tinker: Young at Heart” and a free bear ornament craft station for kids on 12/7 during stroll hours between 5-7 pm

Don Memo, 90 Post Rd East — Complimentary Horchata during stroll hours between 5-7 pm

Earthplace, 10 Woodside Lane — Give the gift that lasts all year long, get an Earthplace t-shirt (new colors and styles) with every new membership all day on 12/7

ELEVEN11, 8 Church Street South — 11% off on 12/7 during stroll hours between 5-7 pm

Faherty, 26 Main Street — Auburn Permanent Jewelry Pop-Up on 12/7 during stroll hours between 5-7 pm

Fred, 30 Post Rd East — Complimentary holiday treats on 12/7 until 6 PM

Glowbar, 33 Elm Street — $10 off for Glowbar facials (non-members only) through 12/31

Head to Tail Books, 132 Compo Rd South — 15% off online purchases with code "STROLL" through 12/20

Hummingbird Healing Center, 57 Main Street, 2nd Fl — Complimentary hot chocolate and tea plus free 10-minute sessions in the Harmonic Egg® on 12/7 during stroll hours 5-7 pm

Huntington Learning Center, 272 Post Rd East — Stop by their booth to enter to win an amazing Holiday Basket filled with goodies to brighten up your season! They are also offering $100 off your Academic Evaluation—perfect for setting educational goals for the New Year. All during stroll hours between 5-7 pm

J. Crew, 145 Main Street — Gift with purchase over $150 on 12/7

Jenni Kayne, 15 Myrtle Avenue, Suite 1 — 15% off and hot chocolate on 12/7 during stroll hours between 5-7 pm

Jeweled Coquette, 46 Post Road East, 2nd Floor, Suite 7 — Visit the studio for an express permanent bracelet from Emily and enjoy some sweet treats while you're there on 12/7 during stroll hours between 5-7 pm

Joe's Pizza, 190 Main Street — Free Garlic Knots (3 per person) on 12/7 during stroll hours between 5-7 pm

Johnny Was, 81 Main Street — $50 off a purchase of $300 or more on 12/7 during stroll hours between 5-7 pm

Kerri Rosenthal, 181 Main Street — 20% off on 12/7 during stroll hours between 5-7 pm

La Beaute Artistry, 234 Post Rd East — 10 to 20% off voucher cards on 12/7 during stroll hours between 5-7 pm

Layla’s Falafel, 1535 Post Rd East — Small fry or soup with a toasted wrap for $16; must mention HOLIDAY STROLL to receive promotion between 5-7pm

Lux, Bond & Green, 136 Main Street —Traveling jewelry cases and holiday treats on 12/7 during stroll hours between 5-7 pm

Madewell, 155 Main Street — Up to 50% off your purchase, gift with purchase, and hot cider on 12/7 during stroll hours between 5-7 pm

Mexicue, 38 Main Street — $10 holiday margarita on 12/7 during stroll hours between 5-7 pm

Middlemarch, 62 Post Road East — Come in, join the mailing list, and be entered to win a $50 Gift Card all day on 12/7

Myr’s Designs, 16 Railroad Place — Red cashmere scarf free with the purchase of $100 all day on 12/7

Naturino Kids Shoes & More, 1096 Post Rd East — 20% off a single item all day on 12/7

Nomade, 150 Main Street — Free S'mores and Holiday chocolate calendar on Main Street on 12/7 during stroll hours 5-7 pm

Office Evolution, 500 Post Rd East, 2nd Floor — All the Starbucks you can drink! Free Private Office until the end of the year while supplies last when you sign a new private office agreement for 6 or 12 months starting 1/1/25. New members only. Deal does not apply to brokers. Promotions are offered all day on 12/7

Old Mill Shell Company, 19 Maple Ave North — Complimentary hot chocolate on 12/7 during stroll hours between 5-7 pm

Party Harty, 578 Post Rd East — 15% off all Westport clothing Sat 12/7 and Sun 12/8

Pizza Lyfe, 833 Post Road East — Complimentary after-dinner dessert on 12/7 during stroll hours between 5-7 pm

Rhone, 7 Main Street — Grace Farms Tea will be in-store offering complimentary tea to customers on 12/7 during stroll hours between 5-7 pm

Rowan, 47 Main Street — Discount coupon, 15% off non-piercing jewelry (excludes diamonds), and enter to win a gift card all day on 12/7

Savvy + Grace, 146 Main Street — Free gift with a purchase of $50 or more on 12/7 during stroll hours 5-7 pm

Scout & Molly's, 283 Post Rd East — 20% off a single item, snacks & drinks all day on 12/7

Sculpt By Sara, 38 Franklin Street — Fitness bands (or something fitness related), a raffle, a hot drink, 15% off packages, and a 1/2 off class to new customers on 12/7 during stroll hours between 5-7

Serena & Lily Westport, 33 Elm Street — Stop by for snacks + drink, plus the opportunity to be entered to win a $500 gift card on 12/7 during stroll hours between 5-7 pm

Serendipity Labs, 55 Post Rd West, 2nd Fl — 20% off all Meeting and Event bookings (before 1/1/25, note: meeting can happen on any date), and Team Room Offices are 50% off the first month on a 6-month agreement OR 50% off 2 months on a 12-month agreement. Promotions run through 1/1/25

SHOE-INN, 21 Main Street — Winter sale, up to 75% all day on 12/7

Sorelle Gallery, 19 Church Lane — Enjoy holiday poinsettia cocktails & treats along with 20% off all in-store and online artwork all day on 12/7; Gift with purchase all day on 12/7

Southern Tide, 33 Elm Street Street — Free gift with purchase wine tote of $150 or more; all day on 12/7

South Moon Under, 14 Post Rd East — 30% off select holiday styles and gifts all day on 12/7

Spice, 8 Sconset Square — Holiday Cocktail Napkins with purchase of $75 or more on 12/7 during stroll hours 5-7 pm.

Splash of Pink, 275 Post Rd East — On 12/7, from 10 am to 5 pm, you can get a free Lilly Pulitzer-printed mug with a $100 purchase or a printed plush blanket with a $300 purchase.

Stephen Kempson London, 5 Post Road West — Hosting female-founded businesses and will be in-store to help you get the perfect gifts for everyone on your list. Enjoy free hot chocolate at their Gift Event all day on 12/7

Studio Cafe, 15 Myrtle Ave — 50% OFF Holiday Lattes (Peppermint Mocha and Peppermint White Chocolate) all day on 12/7

Sundance, 97 Main Street — Receive 30% off your purchase of $100. Sundance will also be hosting Fetch Dog Rescue, where you can find your new furry family member and learn about fostering opportunities. Seasonal cocktails and light bites on hand. All will be available on 12/7 during stroll hours 5-7 pm.

The Bridge at Saugatuck, 541 Riverside Ave — Stop by The Bridge outdoor patio for Complimentary Hot Chocolate & Churros, plus, gift $200 worth of Gift Cards to The Bridge and get a $25 gift card to enjoy for yourself! On 12/7 during stroll hours 5-7 pm

The Clubhouse Westport, 1620 Post Rd East — Opening Jan 2025! Pick up holiday gifts like merch and gift cards, participate in a putting competition, and enter a giveaway to win The Ultimate Clubhouse Experience!

The NEST Agency, 163 Main Street — Small business vendors offering products and complimentary OGGI Ice cream cart on 12/7 from 3 pm to 7 pm

The Sugar Wagon LLC, 30 Berndale Drive — Candy, and if you commit to a party on 12/7, receive 10% off during stroll hours 5-7 pm

The Toy Post, 180 Post Road East — Small gift for each child who comes to the store on 12/7 during stroll hours 5-7 pm

Theory, 87 Main Street — Via Carota Cocktail Tasting (1- 4 pm) and Gift with purchase on 12/7 until 6 PM

Unsubscribed, 33 Elm Street — Special promotion on 12/7 during stroll hours 5-7 pm, TBA

Vince, 115 Main Street — Enjoy a free gift with purchases of $750+, 15% off when you sign up for SMS, and complimentary champagne all day on 12/7

Vuori, 166 Main Street — Free gift with purchases over $250 all day on 12/7

Walrus Alley, 90 Post Road East — Happy Hour specials, which will include Traditional Gluhwein on 12/7 during stroll hours 5-7 pm

WEST Boutique, 117 Post Rd East — Gift with purchase during stroll hours 5-7 pm

West Out East, 1 Main Street — 15% off accessories all weekend

Westport Book Shop, 23 Jesup Rd — Throughout December, purchase a book to donate to Westport Human Services and help spread the love of reading; all shoppers get a coupon during the holiday stroll.\

Williams-Sonoma, 25 Church Lane — Serving their hot apple cider and signature Peppermint Bark on 12/7 during stroll hours 5-7 pm

Yozo Studio, 61 Kings Highway South—Semi-Custom Stationery Special; Select from a list of fonts, colors, and quantities for special pricing. Email hello@yozostudio.com for details. Promotion is available from 11/23 — 12/7