Things to Do in Westport Connecticut

Explore the Westport Country Playhouse

The Westport Country Playhouse is a must-visit for theater enthusiasts.

It hosts an impressive array of performances ranging from classic plays to contemporary dramas.

The Playhouse has a rich history dating back to 1931, offering a cozy yet professional atmosphere.

They have seasons of performances, and you might catch a star-studded cast performing your favorite play.

It’s said that the intimate setting can really enhance your experience, making you feel part of the show.

Relax at Compo Beach

If you’re in the mood for some sun and sand, Compo Beach is perfect.

This beach is spacious, offering plenty of room to spread out and relax.

Families particularly love it here because of the playground and picnic areas.

You might consider going early in the day to secure a good spot, as it can get busy.

It’s also a great place to watch the sunset, giving you a picturesque end to your day.

Explore the Westport Farmers Market

The Westport Farmers Market is a gem for those who love fresh and organic produce.

It’s held every Thursday from May to November, so you’ve got plenty of chances to visit.

You might find everything from locally grown vegetables to artisanal cheeses and homemade bread.

It’s recommended to bring your own bags and arrive early to get the best selection.

The atmosphere is vibrant and community-centric, making shopping here a joyful experience.

Get Lost in the Earthplace Nature Discovery Center

For nature lovers, the Earthplace Nature Discovery Center is a must-visit.

This center offers interactive exhibits, live animal habitats, and miles of trails.

It’s a great spot for families, as kids can learn about local wildlife and ecosystems.

You might bring your camera, as the trails are particularly beautiful in the fall.

Earthplace also hosts events like nature walks and educational workshops throughout the year.

Visit the Westport Historical Society

If you’re a history buff, you’ll love the Westport Historical Society.

The society is home to numerous artifacts and exhibits detailing the rich history of Westport.

You might find special exhibits focusing on different aspects of local history, such as maritime heritage.

They often host lectures and walking tours, which provide deeper insights into the town’s past.

It’s a great way to spend a few hours, especially if you enjoy immersive historical experiences.

Dine at The Whelk

The Whelk is a top dining spot in Westport, known for its seafood-centric menu.

You might try their famous oysters or lobster rolls, which are a hit among locals and tourists alike.

They’re committed to serving sustainable and locally sourced food, which is always a plus.

It’s said that their waterfront location adds to the overall dining experience, offering stunning views.

Reservations are recommended, especially on weekends, as it can get quite busy.

Admire Art at the Westport Arts Center

The Westport Arts Center is a wonderful place to immerse yourself in local and international art.

It features rotating exhibitions, showcasing a variety of artistic styles and mediums.

They also offer art classes and workshops, perfect if you’re feeling creatively inspired.

You might consider attending one of their gallery openings or artist talks for a richer experience.

It’s a haven for art enthusiasts and a great spot to spend a quiet afternoon.

Enjoy Local Brews at the Westport Brewery

If you love craft beer, you should definitely check out the Westport Brewery.

They offer a range of beers brewed on-site, from hoppy IPAs to dark stouts.

It’s a cozy place to relax with friends, and you can even take a tour of the brewery.

You might also enjoy some live music on weekends, which adds to the vibrant atmosphere.

Don’t forget to try their seasonal brews, as they always have something new and exciting on tap.

Take a Stroll in Sherwood Island State Park

Sherwood Island State Park is a fantastic spot for a leisurely walk or picnic.

It offers stunning views of Long Island Sound, making it perfect for nature photography.

The park is spacious, providing plenty of room for various activities like hiking and bird watching.

You might bring a blanket and some snacks for a relaxing afternoon by the water.

The park is open year-round, but it’s especially beautiful in the spring and fall.

Stay at the Westport Inn

If you’re looking for a place to stay, the Westport Inn is highly recommended.

It’s a charming boutique hotel that offers a blend of modern amenities and classic elegance.

The rooms are spacious and well-appointed, providing a comfortable base for your adventures.

It’s said that their on-site restaurant serves delicious meals, which is a nice bonus.

The inn is conveniently located, allowing you to easily explore all that Westport has to offer.

Participate in the Westport Library’s Programs

The Westport Library is more than just a place to borrow books.

They host a variety of programs, from author talks to coding classes and art exhibits.

You might find something for everyone, including children and teens, making it a great family destination.

It’s also a wonderful place to get some work done, with plenty of quiet study spaces and free Wi-Fi.

The library is a cornerstone of the community and a hub of learning and creativity.

Shop at Main Street and Saugatuck

Westport’s Main Street and Saugatuck areas are the heart of shopping in the town.

Main Street is lined with a mix of high-end retailers and charming local boutiques.

You might discover unique, one-of-a-kind items that you won’t find anywhere else.

The Saugatuck area provides a more laid-back shopping experience with artisanal shops and quaint cafes.

If you’re in need of a place to unwind, there are plenty of coffee shops and restaurants to relax in between shopping.

Visit Levitt Pavilion for the Performing Arts

Levitt Pavilion offers an array of performances in an outdoor setting, making it an excellent summer destination.

You might catch everything from local bands to big-name acts, all while enjoying the beautiful riverside location.

The Pavilion offers free concerts, which makes it perfect if you’re looking for budget-friendly entertainment.

It’s recommended to bring a blanket or lawn chairs to make your experience more comfortable.

The relaxed, family-friendly atmosphere makes it great for an evening out with loved ones.

Explore Winslow Park

Winslow Park is a popular destination for outdoor enthusiasts in Westport.

You might take advantage of its walking trails, which are perfect for a leisurely stroll or a more intense hike.

The park is also pet-friendly, so it’s an excellent place to bring your furry friends.

It’s said that the park is particularly beautiful in the fall when the leaves change color.

Meanwhile, in the winter, it’s a great spot for sledding and snow play.

Spend a Day at Connecticut Water Activities

Westport offers a variety of water-based activities, perfect for a fun day out.

You might try kayaking or paddleboarding on the Saugatuck River.

Renting equipment is easy, with several local vendors available to supply what you need.

It’s a fantastic way to get some exercise while taking in the beautiful surroundings.

If you prefer a more relaxed experience, you could take a scenic boat tour around the area.

Indulge in Local Cuisine at Artisan Restaurant

Artisan Restaurant in Westport offers a farm-to-table dining experience that’s hard to beat.

You might try local delicacies prepared by expert chefs committed to using fresh and seasonal ingredients.

The restaurant’s ambiance is cozy and inviting, making it perfect for any occasion.

It’s said that their outdoor seating area is fantastic during the warmer months.

Make sure to make a reservation in advance, as the restaurant can get quite busy.

Enjoy the Annual Yankee Doodle Fair

If you’re in town during the summer, you might want to check out the Yankee Doodle Fair.

This annual event offers rides, games, food stalls, and live entertainment for all ages.

It’s a community staple, bringing together residents and visitors alike for a weekend of fun.

Proceeds from the fair support local charities, so you’ll also be contributing to a good cause.

Make sure to bring the whole family; there’s something for everyone to enjoy.

Join a Fitness Class at JoyRide Cycling Studio

If you want to stay active during your visit, JoyRide Cycling Studio offers excellent fitness classes.

You might try one of their high-energy spinning classes to get your heart pumping.

The studio provides all the equipment you need, so there’s no need to worry about bringing your own gear.

It’s said that the instructors are incredibly motivating, making it easier to push through a tough workout.

Schedules are flexible, and you can usually find a class that fits into your day’s plans.

Stroll Through Old Mill Beach

A visit to Old Mill Beach offers a quieter, more serene beach experience in Westport.

It’s a great spot to take a peaceful walk and enjoy the waterfront views.

The beach is less crowded than Compo, making it ideal for those who prefer a little more solitude.

Packing a picnic can enhance your experience, allowing you to enjoy a meal with an ocean backdrop.

It’s also a great spot for kayaking, so consider renting one if you’re up for a little adventure.

Stop by the Morris Jesup Memorial Library

The Morris Jesup Memorial Library is a cornerstone of Westport’s community life.

Along with an extensive collection of books, the library offers numerous events and programs.

You could attend one of their author talks or art exhibitions to enrich your visit.

The library also features tranquil reading areas, making it a great place to unwind with a good book.

They offer free Wi-Fi and various workspaces, offering a quiet place if you need to get some work done.

Walk the Westport Riverwalk

The Westport Riverwalk offers a scenic and leisurely stroll along the Saugatuck River.

It’s a perfect way to enjoy the beauty of the town while getting some light exercise.

You might find local wildlife along the way, making it a delightful experience for nature enthusiasts.

The path is well-maintained and easily accessible, suitable for all ages.

Consider ending your walk at one of the nearby cafes for a refreshing drink or snack.

Explore Westport’s Boutiques and Antique Shops

Westport is home to a variety of charming boutiques and antique shops.

You might discover unique fashion pieces, home décor, and vintage finds that make perfect souvenirs.

It’s suggested to take your time browsing as each shop offers something different and special.

The shop owners are often locals, making it a wonderful way to support the community.

Shopping in Westport adds a personal touch to your visit, offering more than just commercial retail experiences.

Picnic at Winslow Park

A picnic at Winslow Park can be a delightful way to spend a sunny afternoon.

The park has several picnic tables and open lawns where you can relax and enjoy a meal.

You might pack a basket full of your favorite treats and find a cozy spot under the shade of a tree.

The park’s serene environment and natural beauty make it perfect for a relaxing day out.

It’s also a great spot for kids to run around and play.

Discover Local History at Sherwood Island State Park

Sherwood Island State Park is a must-visit for history enthusiasts interested in local heritage.

The park is Connecticut’s first state park and has a fascinating history dating back to the early 20th century.

You might explore the park’s memorial area, which pays tribute to the victims of 9/11.

The interpretive exhibits offer insights into the park’s natural and cultural history.

It’s a place where you can enjoy both nature and a bit of historical learning in one visit.

Attend Workshops at Westport’s Public Schools

Westport’s public schools often host workshops and events open to the community.

These events range from educational seminars to cultural performances and are a great way to immerse yourself in local life.

You might find workshops on topics like art, technology, or wellness.

Attending these events can be a great way to learn something new while meeting locals.

Check the local school district’s website for upcoming events during your visit.

Take a Boat Tour from Westport Marina

The Westport Marina offers various boat tours that allow you to explore the town from a different perspective.

You might choose a sunset cruise, which offers stunning views of the coastline at golden hour.

Fishing charters are also available if you’re interested in a more hands-on experience.

It’s said that the tours provide excellent opportunities for photography and relaxation.

Booking in advance is recommended, especially during peak tourist season.

Explore the Nature Trails at the Devil’s Den Preserve

The Devil’s Den Preserve offers over 1,700 acres of hemlock, oak forests, and wetlands.

It’s the perfect place for those who enjoy hiking and nature walks.

You might choose from several trails, each varying in difficulty and length.

The preserve is home to diverse wildlife, so keep an eye out for birds and small mammals.

Visiting in the fall is particularly beautiful when the leaves change color.

Visit the Westport Historical Society’s Wheeler House

The Wheeler House, part of the Westport Historical Society, offers a glimpse into 19th-century life.

This beautifully preserved house features period furnishings and exhibits that tell the story of past residents.

You might take a guided tour to learn more about the architecture and history of the house.

The society often hosts special events and lectures focusing on various historical topics.

It’s a must-visit for anyone interested in local history and heritage.

Try Paddleboarding on the Saugatuck River

Paddleboarding on the Saugatuck River is a fun and active way to explore Westport’s waterways.

Several local vendors offer paddleboard rentals and lessons for beginners.

It’s an excellent workout and provides a unique vantage point of the town.

The calm waters of the river make it suitable for all skill levels.

You might consider an early morning session when the water is particularly serene.

Enjoy Live Music at MoCA Westport

MoCA Westport often hosts live music events that are a treat for the ears.

You might catch performances ranging from jazz and classical to contemporary genres.

The museum’s intimate setting makes for a fantastic live music experience.

Check their event calendar in advance to see what’s on during your visit.

It’s a great way to combine an appreciation for visual and musical arts.

Explore Boutique Shopping in Downtown Westport

Downtown Westport is a shopper’s paradise with its array of unique boutiques and specialty stores.

You might find one-of-a-kind clothing, jewelry, and home decor items.

The downtown area’s charming atmosphere makes for a pleasant shopping experience.

It’s said that many of these boutiques are run by local artists and craftsmen.

Spending an afternoon here supports small businesses and adds a personal touch to your shopping spree.

Discover Local Treasures at the Westport Antiques Center

The Westport Antiques Center is a haven for collectors and treasure hunters.

You might find everything from vintage furniture and jewelry to rare collectibles.

Browsing the center’s extensive offerings can be an enjoyable way to spend a few hours.

It’s a place where you never know what unique item you might stumble upon.

Antiquing here gives you a sense of Westport’s rich heritage and artistic roots.

Attend a Yoga Class at Double Diamond Holistic Health

Double Diamond Holistic Health offers a variety of yoga classes suitable for all levels.

It’s a great way to relax and rejuvenate during your visit to Westport.

The center also offers holistic health services like acupuncture and massage.

Classes often incorporate mindfulness and meditation, adding to the overall wellness experience.

You might find that a session here leaves you feeling balanced and refreshed.

holistic health

Tour the Westport Permanent Art Collection

Westport’s Permanent Art Collection includes works displayed across public buildings and schools.

You might join a guided tour to learn more about the artists and their works.

The collection includes pieces by notable artists, offering a glimpse into Westport’s cultural landscape.

It’s a wonderful way to appreciate art while exploring various parts of the town.

The collection highlights the town’s commitment to fostering creativity and culture.

Visit Local Craft Fairs and Artisan Markets

Westport hosts several craft fairs and artisan markets throughout the year.

You might find handmade crafts, local art, and unique gifts at these events.

The markets provide an opportunity to meet local artisans and learn about their work.

They’re community-oriented events, making them a fun and engaging activity for all ages.

Whether you’re looking to shop or just browse, these markets offer a delightful experience.

local coffee houses

Participate in a Wine Tasting at the Westport Winery

The Westport Winery offers wine tastings featuring their local selections.

You might try a flight of wines accompanied by cheese and charcuterie boards.

The winery’s knowledgeable staff can guide you through the tasting, offering insights into each wine’s profile.

It’s a relaxing way to spend an afternoon, especially for wine enthusiasts.

Consider bringing home a bottle or two to remember your visit by.

premier hotels

Explore Westport’s Performing Arts Scene

Westport has a vibrant performing arts scene with several theaters and venues hosting live performances.

You might catch a play or musical at the Westport Community Theatre.

Their productions are known for their high quality and engaging performances.

The Levitt Pavilion for the Performing Arts offers outdoor concerts and events, perfect for a summer evening.

It’s a great way to enjoy live entertainment while supporting local artists.

Enjoy Fresh Seafood at the Black Duck Café

The Black Duck Café is a local favorite for fresh seafood and a laid-back dining experience.

Located on the water, the café offers a unique and cozy atmosphere.

You might try their famous burgers and clams, which come highly recommended.

The casual, bar-like setting makes it a great spot for a relaxed meal with friends.

It’s said that this spot feels like a hidden gem, tucked away from the bustle of town.

Discover the Children’s Library at the Westport Library

The Westport Library is not just for adults; it has a fantastic Children’s Library as well.

You might find an array of books, interactive exhibits, and educational games for kids.

The library often hosts storytime sessions and activities tailored for young readers.

It’s a great place to nurture a love for reading and learning in children.

Parents will appreciate the safe and engaging environment for their little ones.

Take a Scenic Drive along the Connecticut Coastline

A scenic drive along the Connecticut coastline offers breathtaking views and charming stops.

You might include stops at local beaches, parks, and historic landmarks along the way.

It’s an excellent way to explore the region at your own pace.

Consider planning your drive during sunset for particularly stunning views.

Don’t forget to bring a camera to capture the beautiful landscapes.

Attend the Annual Westport Film Festival

The Westport Film Festival celebrates independent films from around the world.

The festival showcases a variety of genres, offering something for everyone.

You might meet directors, actors, and fellow film enthusiasts during screenings and discussions.

It’s an exciting event for anyone passionate about cinema.

Check the festival’s schedule in advance to plan your visit around must-see films.

Explore the Gardens at the Westport Historical Society

The gardens at the Westport Historical Society are a tranquil and beautiful place to explore.

You might find a variety of flowers, plants, and picturesque walking paths.

The gardens are meticulously maintained, providing a peaceful retreat in the heart of town.

It’s a perfect spot for a leisurely stroll or to simply sit and enjoy the surroundings.

Visiting in the spring or summer offers the best floral displays.

Shop at the Seasonal Pop-up Markets

Westport hosts seasonal pop-up markets featuring a mix of vendors selling local and artisanal products.

These markets offer everything from fresh produce and baked goods to crafts and unique gifts.

You might discover new local businesses and products at these vibrant events.

The markets create a lively and festive atmosphere, especially during holidays.

They’re a great place to pick up a souvenir or a special treat.

Join a Book Club at the Westport Library

If you enjoy reading and discussing books, consider joining one of the Westport Library’s book clubs.

The library hosts various book clubs catering to different interests and age groups.

You might find it a great way to meet new people and engage in intellectual discussions.

Reading the book ahead of time makes for a more enriching experience.

Check the library’s website for book club schedules and reading lists.

Explore Local Art at the William H. Pitt Center

The William H. Pitt Center often features local art exhibitions and events.

It’s a wonderful place to see the work of local artists and craftsmen.

The center hosts a variety of cultural events, including live music and theater performances.

You might find yourself inspired by the creativity and talent on display.

Exploring the center offers a deeper appreciation for Westport’s vibrant arts scene.