In just 3 years, the “06880” Holiday Stroll has become a beloved tradition.
Now — with a big boost from the Westport Downtown Association — the 4th annual event will be way bigger, and even more fun.
For example: a DJ at Brooks Corner. Vendors on Elm Street. A new Westport Police Department’s Toys for Tots collection box.
Mark your calendar now for Saturday, December 7 (5 to 7 p.m.).
All the favorite attractions return, including Santa, face painting, s’mores, a photo booth, holiday music from Staples High School’s elite Orphenians, and Staples Players costumed characters.
It’s a month away, but already nearly 2 dozen retailers, restaurants and others have signed on, with gifts, giveaways, discounts and more.

The Staples Orphenians, always a Holiday Stroll favorite.
It’s a town-wide event, with participation from merchants on Post Road West and in Saugatuck too. Some are offering specials all day, all weekend — even through December 31.
They include:
Bella Bridesmaids: Champagne bar (all day)
Castle Wine & Spirits: Free tote bag with purchase; get 5% off applicable wines when used in the future (all day)
Cove Collective: 15% off, and festive treat (all day)
Crafty Kids Westport: Arts and crafts station
Glowbar: $10 off facials for non-members (through December 31)
Hummingbird Healing Center: Hot chocolate and tea, plus free 10-minute session
Jenny Kayne: Hot chocolate; 15% off
Kerri Rosenthal: 20% off
Lux Bond & Green: Traveling jewelry cases and holiday treats
Naturino Kids Shoes: 20% off single item (all day)
Savvy + Grace: Gift, with purchase of $50 or more
Serendipity Lab: Discounts on rooms and meetings (through December 31)
Studio Cafe: 50% off holiday lattes and peppermint mocha lattes (all day)
The Clubhouse: TBD
Theory: Via Carota cocktail tasting (1-4 p.m.); gift with purchase (all day)
Unsubscribed: Special promotion
Walrus Alley: Happy hour specials, including traditional Gluhwein
West Out East: 15% off all accessories (all weekend)


Are they finally going to close that stretch of Main Street to car traffic for this year? Last year I almost felt like I was just wandering down a thru-street, much as I loved it.
Wow Dan, is this an AI reply?
If so, don’t forget, ‘…donate to…”
I’m going to be a vendor and I can’t wait! Love that I can help support this awesome work that Dan does for this community!