Why has it taken me this long to visit Westport?

This is the question I kept asking myself a few weeks ago when I finally visited this adorable town in Connecticut. I had wanted to take a trip in the past but never had an occasion or reason to visit until I scheduled an appointment at a bridal boutique there.

It’s about 40 minutes from my family home in Westchester so we drove up last Sunday with the intention to explore the town a bit before heading home.

Westport is a seaside town on the Long Island Sound, nestled between Norwalk and Fairfield. The town center is sizable but quiet, and unbelievably charming. I never wanted to leave! There is no shortage of restaurants to dine and

Shopping & Restaurants in Town

This is the cutest commercial district, with so many great small businesses and boutiques as well as some of my favorite chain stores! The same is true for the restaurants in Wesport, where some names are recognizable others are small businesses unique to the town!

Restaurants

Bartaco Wesport - can’t have a bad meal at a Bartaco! Another great seaside location
Walrus Alley - First on my list for the next visit!
The Cottage
Spotted Horse Tavern
Basso. Bistro
Amis Trattoria
The Whelk
Black Duck Cafe

If you’re looking for something quick but filling check out Rye Ridge Deli ! I love stopping there in Stamford. For something healthy swing by Green and Tonic. For a sweet treat before you head home stop by Donut Crazy in Saugatuck, by the train station.

Popular Shops

There are many more stores in the wider Westport area, but here are some of my favorite shops right on Main Street and Post Rd in the main commercial district.

Anthropologie Westport - It’s huge!!! Literally bigger than the NYC flagship.
South Moon Under
Madewell
Lululemon
Intermix
Bluemercury
Pottery Barn
Serena & Lily
West Elm
Barnes & Noble

There is also a Williams Sonoma, Marine Layer, Athleta, Theory, Barbour, Paper Source, Vince, Gap, Urban Outfitters, Patagonia, J. Crew, Brooks Brothers, Tiffany’s - and that’s not all! I could spend all day here! And even after shopping all day, you might not make it to every business.

Small Businesses

Workout Studios

Terrain

I was familiar with the Pennsylvania locations of Terrain that had been around for a while but didn’t realize how much closer to home this shop is! If you’re spending a day in Westport, I highly recommend planning a stop at Terrain.

Plants, home decor, beauty and skincare, gifts, a restaurant with delicious food, and a wine and cocktail list all under one roof! What more could I ask for?

I can’t wait to go back later this Spring when everything is in bloom outside in the garden and nursery as well!

The Indoor Nursery

Shopping for the Home

Lunch at Terrain

If you’re visiting Westport and haven’t been to Terrain before I really recommend planning a shopping trip around a meal at Terrain!

CUTENESS overload

The whole town is adorable, and they have a ‘bookcycle’ for recycling books in Bedford Square in town and I just fell in love and told my Mom and sister to leave me here.