One of the best things about living in Fairfield County is that you don't have to fight mall traffic or spend hours scrolling online to find thoughtful gifts. Our towns come alive this time of year with pop-up markets, local makers, and longtime charity sales that double as neighborhood reunions.
If you are around Westport and Weston this weekend, November 13 through 15, there are three wonderful local shopping events worth putting on your calendar.
1. Main Street Weston Holiday Market (Friday, Nov 13 & Saturday, Nov 14)
Hosted by the Weston Women’s League at St. Francis of Assisi Church on Norfield Road, this 14th annual event brings more than 30 local makers, brands, and boutiques together under one roof. Even better, proceeds go right back into the community to support the Weston Warm-Up Fund and Weston Human Services.
Friday Night Opening Party (7:00 PM to 10:00 PM): An adults-only evening featuring cocktails, a bourbon tasting, a grazing table, and first dibs on the shopping before the Saturday crowds.
Saturday Shopping (10:00 AM to 3:00 PM): Grab a coffee from the coffee truck, browse the Honey Bee Flower Truck, enjoy a mimosa, and knock out your gift list.
2. Westport Woman’s Club Annual Clothing & Accessories Sale (Friday, Nov 13 to Sunday, Nov 15)
If you love the thrill of a great treasure hunt, the Westport Woman’s Club on Imperial Avenue is hosting their epic multi-day sale all weekend long. You will find racks of women's and men's clothing, boots, handbags, scarves, and jewelry, with every dollar raised supporting local charities and nonprofits across Fairfield County.
Pro Tip: They offer Early Bird shopping on Friday morning from 9:00 AM to 10:00 AM for a $10 donation if you want first pick of the best pieces. And if you swing by on Sunday between 11:00 AM and 4:00 PM, everything left is half price.
3. Popshop Holiday Market at the Westport Museum for History & Culture (Sunday, Nov 15)
Wrap up your weekend on Sunday from 10:00 AM to 4:00 PM at 25 Avery Place. Popshop Market curates an awesome mix of independent retailers selling handcrafted jewelry, home decor, vintage finds, and unique seasonal gifts you won't see in big-box stores. Plus, the museum is running their Fall Harvest Bake Sale at the exact same time, so you can pick up fresh treats for Sunday dinner while you browse.
The Marion Filley Team Perspective
When clients ask me what it really feels like to live in Westport or Weston, I always point to weekends like this. It isn't just about the houses. It is about showing up for local makers, supporting neighbors who volunteer their time to run these events, and running into familiar faces over a cup of coffee.
