Top Things to Do in Westport

Introduction : Top Things to Do in Westport | Your Ultimate Guide to This Coastal Gem

Hey there, fellow travelers! Ever found yourself wondering what to do in the charming coastal town of Westport? Well, you’re in luck because I’ve spent plenty of time exploring this gem and I’m excited to share my favorite spots and activities with you. Whether you’re planning a weekend getaway or a longer stay, Westport offers something for everyone – from stunning beaches and historic sites to mouthwatering restaurants and unique shopping experiences.

Soak Up the Sun at Compo Beach

Let’s kick things off with what might be Westport’s crown jewel – Compo Beach. This gorgeous stretch of coastline is perfect for those lazy summer days when all you want to do is feel the sand between your toes and listen to the waves crash against the shore.

What makes Compo special? For starters, the views are absolutely killer. On clear days, you can see all the way to Long Island across the Sound. The beach is well-maintained with clean facilities, a concession stand for when hunger strikes, and plenty of parking (though FYI, you’ll need a permit during peak season).

My personal favorite spot is near the cannon monuments – they’re remnants from the Revolutionary War and add a cool historical touch to your beach day. Ever wondered what it would be like to watch a sunset while sitting on a piece of American history? Here’s your chance!

Explore the Scenic Sherwood Island State Park

If you’re anything like me and prefer your beaches with a side of nature trails, Sherwood Island State Park is your spot. As Connecticut’s first state park, it’s got some serious credentials, and trust me, it lives up to the hype.

The park offers more than just beaches – there are walking trails, salt marshes, and woodlands to explore. Birdwatching here is phenomenal, especially during migration seasons. I once spent an entire morning just watching ospreys dive for fish – nature’s own fishing tournament, and way more exciting than it sounds!

There’s also a moving 9/11 memorial that offers a quiet place for reflection with a beautiful view of the New York skyline across the water. It’s simple yet powerful – definitely worth a visit.

Step Back in Time at the Westport Historical Society

History buffs, this one’s for you! The Westport Historical Society (now officially called the Westport Museum for History & Culture) is housed in a charming 1795 Federal-style home right in downtown. They do an amazing job of bringing the town’s past to life through engaging exhibits.

What I love about this place is how they connect historical events to the present day. It’s not just dusty artifacts in glass cases – they tell stories that make you understand how Westport evolved from a small farming community to the arts-focused town it is today.

They often host walking tours of the downtown area too, which is a fantastic way to learn about the architecture and hidden history of the buildings you might otherwise walk right past. Did you know Westport was once a major onion farming center? Random facts like these make me unreasonably happy. 🙂

Browse the Westport Farmers’ Market

Thursday mornings in Westport mean one thing for locals: farmers’ market time! Located at the Imperial Avenue parking lot, this isn’t your average produce stand setup – it’s a full-on food festival that happens weekly.

The vendors here are passionate about what they do, and it shows in the quality of their offerings. From just-picked veggies and artisanal cheeses to homemade pastries that will ruin all other baked goods for you forever, this market is a food lover’s paradise.

My strategy? Grab a coffee from one of the local roasters, pick up some fresh bread and cheese, maybe snag a sweet treat (the maple cookies are to die for), and head to the nearby Saugatuck River for an impromptu picnic. Market days are definitely my happy days!

Catch a Show at the Westport Country Playhouse

Ever since 1931, the Westport Country Playhouse has been the heart of the town’s thriving arts scene. Housed in a converted 1835 tannery building, this theater has an impressive legacy that includes performances by some of the biggest names in American theater.

What’s really cool about the Playhouse is that it’s not just for tourists – it’s a genuine cultural hub for locals. The programming ranges from classic plays to contemporary works, with something to suit all tastes. I’ve never seen a bad production here, and that’s saying something!

Pro tip: Check their schedule well in advance of your visit and book tickets early. The best shows sell out fast, and you definitely don’t want to miss out on experiencing a performance in this historic venue.

Stroll Down Main Street and Shop ‘Til You Drop

Westport’s Main Street is what small-town shopping dreams are made of – a perfect mix of high-end retailers, local boutiques, and unique specialty shops. It’s the kind of place where you might pop in “just to look around” and emerge three hours later with bags full of treasures you never knew you needed.

What makes shopping here different from your average mall experience is the personal touch. Store owners and staff actually want to help you find exactly what you’re looking for, and they’re full of recommendations for other places to check out in town.

My favorite stops include Savvy+Grace for unique gifts and home accessories, The Plumed Serpent for when I need to pretend I can afford fancy things, and Westport Book Shop for used books that always seem to include exactly the title I’ve been meaning to read.

Paddle Along the Saugatuck River

One of my absolute favorite ways to experience Westport is from the water. The Saugatuck River winds through town, offering a different perspective on familiar landmarks and access to hidden spots you can’t reach by car.

There are several places to rent kayaks or paddleboards, but Downunder is my go-to. Their guides know all the best routes, whether you’re looking for a peaceful nature paddle or want to explore the downtown waterfront. Ever seen a heron fishing just a few feet away from you? It’s pretty magical.

If you’re visiting in warmer months, consider taking a sunset paddle – the way the light hits the water and the buildings along the shore is absolutely gorgeous. Just remember to bring a waterproof bag for your phone because those sunset photos are definitely Instagram-worthy!

Indulge in Culinary Delights

Westport’s food scene has seriously upped its game in recent years, and now boasts everything from casual waterfront seafood joints to upscale dining experiences that would impress even the pickiest foodie.

For breakfast, you can’t beat Coffee An’ Donut Shop – their chocolate frosted donuts have a cult following for good reason. Trust me, get there early before they sell out!

Lunch options abound, but The Whelk is my personal favorite for fresh seafood with a view of the Saugatuck River. Their lobster roll might be the best I’ve ever had (and I’ve had A LOT of lobster rolls in my day).

For dinner, it’s hard to choose just one place, but Kawa Ni offers an incredible Japanese pub experience with small plates that will blow your mind. The bao buns are life-changing – I’m not exaggerating!

Take in Art at the MoCA Westport

The Museum of Contemporary Art Westport (formerly the Westport Arts Center) showcases cutting-edge exhibitions that often feature both international artists and local talent. What I appreciate most about this space is how accessible they make contemporary art – the staff are great at explaining concepts without making you feel like an art dummy.

They also host fantastic concerts, educational programs, and workshops throughout the year. The building itself is worth checking out too – a beautifully renovated industrial space that perfectly complements the artwork it houses.

Even if you’re not usually a museum person, I’d recommend giving MoCA a shot. It’s the kind of place that might just change your mind about contemporary art. And if not, their events often include wine, so there’s that. :/

Hit the Trails at Earthplace

Need a nature fix? Earthplace, The Nature Discovery Center, offers over 62 acres of open space with trails that wind through forests, meadows, and alongside streams. It’s a peaceful retreat just minutes from downtown Westport.

What makes Earthplace special is their commitment to environmental education. The nature center houses rescued animals that can’t be released back into the wild, and meeting these animal ambassadors up close is an awesome experience for kids and adults alike.

My favorite time to visit is early morning when the trails are quiet except for birdsong. There’s something about starting your day with a forest bath that just sets the right tone. Plus, their butterfly garden in summer is absolutely spectacular!

Catch a Sunset at Compo Beach Cannons

I’m circling back to Compo Beach to end our tour, but this time for a very specific reason – sunset at the cannons is hands-down one of the most beautiful experiences Westport has to offer.

There’s something almost cinematic about watching the sun sink below the horizon, painting the sky in pinks and oranges, while sitting beside these historic monuments. It’s one of those perfect moments that reminds you why travel is so worthwhile.

Bring a blanket, maybe some cheese and crackers (and wine if that’s your thing), and simply soak in the beauty. It’s the perfect way to cap off a day of exploring Westport.

Final Thoughts

Westport may not be as famous as some other New England coastal towns, but that’s part of its charm. It offers a perfect blend of natural beauty, cultural experiences, and small-town hospitality that makes for an unforgettable visit.

Whether you’re a beach bum, history enthusiast, foodie, or art lover, you’ll find something to love in this vibrant community. So what are you waiting for? Pack your bags and come see what makes Westport special – I have a feeling you’ll be planning your return trip before you even leave!

Have you been to Westport before? What were your favorite spots? I’d love to hear about your experiences and maybe discover some new gems for my next visit!