This Westport, Connecticut Shopping Guide will give you a glimpse into this popular waterfront town. The downtown area of Westport is a lively place to eat and shop in Southwestern Connecticut. It has a great waterfront location and there are a ton of things to do. In this post I will list the offerings of a few main streets within the downtown area. Along the way, I will highlight a few of the local small businesses.

Westport Connecticut Shopping on Main Street (Clothes & Shoes)

These stores are located in between the Saugatuck River and Main street. Experience a wonderful water view behind the stores.

Whenever I stop on Main Street I make sure to visit the GAP. This location is three stories with every single department all in one place. Think the GAP sportswear lines and GAPBody as well.

Great places to pick up work clothes are Talbots, Madewell and J. Crew. One thing I like about the shops on this side of Main Street is that the stores have entrances on both ends. This means each store faces both Main Street and the waterfront. You don’t have to walk all the way around the strip mall. The two images below show the front and back entrances of Shoe-In (the turquoise store fronts) and Loft.

Shoe-Inn has been in business since 1972 and has locations in both New York and Connecticut. The owners, the Lawson family come from four generations of shoemakers. This history dates back to the late-1940s. What sets them apart is working with six Italian shoe designer brands that produce lines of shoes exclusive to Shoe-in.

If you’re looking for furniture head over to West Elm or Pottery Barn.

On the corner of Main Street and the Post Road is the giant flagship Anthropologie store. The store is huge and it’s a mix of great architecture and design. All of this is housed in a charming Tudor-style building.

Post Road East (Gifts & Jewelry)

The Post Road East is a great place to buy gifts for the luxury lover in your life. Think Tiffany and Co, The Cashmere Sale, and more.

The Cashmere Sale is a pop-up shopping event that takes place in 30 locations nationwide. One of them happens to be Westport, Connecticut. It started from a small get together of like-minded friends in a Greenwich Connecticut living room. That was 20 years ago. They offer online shopping and limit their pop-up stores to once a year. By getting rid of their overhead expenses, the goal is to pass the savings onto their customers. Email them at westport@thecashmeresale.com for sale dates and updates.

Fig Linens and Home is a home store that sells luxury bedding and linens. They offer a lot of unique items, many imported from places like France and India. Also check out their custom bedding and custom bath items. Summer 2023 Update: Fig Linens and Homes is no longer located on Post Road East. Find them located steps away at 7 Church Lane.

You can find gifts for the book lover at Barnes & Noble. There’s another great book store that I talk about later in this post. Keep reading for that. I actually prefer it to Barnes & Noble.

Jesup Rd (Books and more)

Green and Tonic is a little café and juice bar. My sister bought a really good smoothie with dragon fruit. They have lots of vegetarian options such as meatless sausage, egg and cheese sandwiches. There are also lots of little pastries.

The Westport Bookshop is a quaint little used bookstore. Also purchase books online. They have a good variety of used books, CDs, DVDs, records and more. I love the atmosphere of the bookstore. It is cozy, yet well lit and organized. The associates are very friendly and helpful. While there I picked up a travel book about India.

Step over to the other side of Jesup Road and head to the Westport Public Library. This is a great modern library on a gorgeous location. I used to use it as a remote work location a few years back. Expect a very nice environment with a bright and airy interior space. Located inside the library is the WPL Café for when you’re looking for a little bite to eat.

Jesup Green is located in front of the library. It’s a cute little park I sat in the other day. They also have a small sculpture garden. In front of the park there are even more gorgeous water views. Lots of benches are available to sit and enjoy the scenery. 

This Westport Connecticut shopping guide gives just a taste of all the places to visit in Downtown Westport. Come and see the rest for yourself!