Having grown up in Fairfield County, Connecticut, I’ve been extremely fortunate enough to take advantage of all that its Gold Coast has to offer. From its beautiful beaches to its historic colonial homes, just about everything in this area is picture-perfect. Located just one hour from the hustle and bustle of New York City, the town of Westport is one of my favorites to spend a day in, especially when the weather starts to get warmer. Its idyllic and picturesque charm is every photographer’s dream and a real treat for locals and visitors alike. It’s no wonder a number of celebrities like Martha Stewart and Paul Newman called it home for many years.
What I find to be most appealing about Westport is its size as well as the variety of landscapes and activities that it has to offer. It’s small enough that you get the vibe of a quaint New England town, but big enough that there’s plenty to explore in a day or a weekend. If you want to go to the beach, there is a handful of beautiful ones to choose from. If you want to go shopping, it has almost every store you can think of downtown. If you enjoy the theater and are in the mood to see a show, the historic Westport Country Playhouse provides Broadway-quality shows for a fraction of the price. Keep reading to see my own personal list of must-do’s on a day trip to Westport!
To start my day, I’ll head to either the Granola Bar or Tavern on Main for a delicious brunch. While near Main Street, I’ll check out the multitude of stores that are in town and do some shopping – they have everything from Brooks Brothers to lululemon, with some great local businesses scattered throughout as well. From there, I’ll make my way to the Inn at Longshore , which has a golf course, restaurant/event venue, tennis courts, marina, and even a sailing school! After taking a stroll on the beach and around the marina, I’ll grab a light lunch at Pearl, the restaurant on premises, and enjoy a stunning view of the Long Island Sound (their brunch is also fantastic – the Nutella cinnamon rolls are to die for!)
From there, I’ll head to Westport’s Compo Beach, which some have called the “best beach in Fairfield County.” Sherwood Island State Park is also a great spot to catch some rays on a sunny day. Before wrapping up for the day, I’ll take a drive through town and admire the gorgeous historic homes that line many of the main roads. For dinner, I’ll decide between Bartaco and the Spotted Horse Tavern, both known for their excellent food (though I will always have a soft spot for Bartaco). If you’re like me and you like to have something sweet after dinner, Saugatuck Sweets has awesome ice cream and a ton of candy to choose from.
Thanks for following along as I shared some of my favorite things to do in Westport. If you ever have the opportunity to make the trip, I hope you do – it’s a New England gem!
Does anyone else get sad (read: devastated) when it’s time for the Christmas tree to come down? I don’t know about you, but it’s one of the worst feelings for me! November and December is a time filled with such joy and festivity, and when that all comes to an end, it can feel a little abrupt.