Things to Do in Weston Connecticut
Updated June 18, 2024 at 3:30 pm
Discover the best activities and attractions in Weston, Connecticut, from scenic parks and nature reserves to unique local shops and dining options in this comprehensive guide.

Unwind in Weston Woods: Hiking and Nature Walks
Weston Connecticut is a haven for nature enthusiasts. The town is wrapped in lush greenery, offering a series of scenic trails and nature walks that you can totally soak in. One must-visit spot is the Devil’s Den Preserve.
The Devil’s Den Preserve spans over 1,700 acres. It is managed by the Nature Conservancy and features around 20 miles of trails.
If you crave a diverse hiking experience, this is the place to be. You’ll find diverse wildlife and serene landscapes that make each step worthwhile.
Local hikers swear by the Den as a go-to spot for an immersive nature experience.
Relish with Locally Sourced Cuisine
If you’re a foodie, Weston won’t disappoint. The town offers several local eateries that provide delightful culinary experiences.
A local favorite is the Weston Provisions. It’s a deli and market known for fresh, locally sourced foods.
The place has rave reviews for its high-quality sandwiches, fresh salads, and deli meats.
Another gem is the Lachat Town Farm. Though primarily a farm, they host farm-to-table dinners during the summer that incorporate locally grown produce.
Family Fun: Child-Friendly Activities
Weston is also a fantastic place for families. For a memorable outing, head to the Weston Historical Society.
The Society often organizes child-friendly events where kids can learn about the town’s history in an interactive manner.
Parks like the Bisceglie – Scribner Park are perfect for outdoor activities. They come equipped with playgrounds, ball fields, and a pond for fishing. Local families find this park a gem, particularly during warmer months.
Art and Culture in Weston
For a dose of culture, the Weston Library often has art exhibitions and cultural events that cater to a broad audience. These exhibitions bring in local artists and provide a platform for community engagement.
Another great spot for art enthusiasts is the Mark Twain Library, just a short drive away in Redding. It’s famous for its annual book fair and a varied calendar of cultural events.
Local Festivals and Annual Events
Weston hosts several annual events that bring the community together. One of the most awaited events is the Weston Fine Arts Festival, typically held in the summer.
The festival features local artists, musicians, and craft vendors, offering a rich cultural experience for attendees. The Weston Memorial Day Parade is another cherished event that fosters community spirit.
If you’re interested in exploring similar experiences, explore some family-friendly attractions in nearby regions for endless fun.
Shopping at Local Boutiques
If shopping is on your agenda, Weston has several charming boutiques. You’ll find unique items ranging from fashion to home décor.
One prominent boutique is Satya Jewelry in Norwalk, which is not too far from Weston. The store offers an exquisite range of jewelry designed with semi-precious stones.
Many locals find its intricate designs and spiritual symbols captivating. Reviews highlight the quality and craftsmanship of their products.
Fitness and Wellness Activities
Residents of Weston pay special attention to fitness and wellness. You’ll find several wellness centers and gyms in the area.
For yoga enthusiasts, a visit to one of the prime yoga retreats in Rhode Island is also worth considering. Weston Pilates Studio offers high-quality pilates sessions tailored to different skill levels.
The studio has a strong reputation for its seasoned instructors and welcoming atmosphere. According to frequent attendees, their personalized approach is a huge plus.
Relax and Rejuvenate at Local Spas
If relaxation is what you seek, Weston’s local spas are a great option. The Adam Broderick Salon & Spa offers a range of services, from massages to skin treatments.
The spa maintains a high rating for its relaxing ambiance and professional staff. Services such as facials and massages are particularly recommended by patrons.
Exploring Weston’s Historical Sites
Dive into history by visiting the Norfield Historic District. This area features numerous buildings dating back to the 18th century. Walking around feels like going back in time, with fascinating insights into Weston’s past.
Weston Historical Society is another must-see for history buffs. This vibrant institution keeps the town’s history alive with intriguing exhibits and well-preserved artifacts.
If you’re captivated by historical landmarks, you’ll also enjoy exploring some must-see historical landmarks in nearby regions.
Unique Features of Local Shopping Options
When it comes to unique finds, Weston’s farmers’ market deserves mention. The market, typically open from spring to fall, showcases fresh produce, artisanal goods, and handcrafted items.
Patrons vouch for the freshness and quality of the items sold here. The market makes for a delightful shopping experience while supporting local farmers and artisans.
To explore more, consider visiting some of the top farmers’ markets in nearby Rhode Island.
A Taste of Elegance: Fine Dining in Weston
If you are in the mood for a luxurious dining experience, Weston has several top-tier restaurants that are sure to impress. One standout option is La Roue Elayne at Cobbs Mill Inn. This elegant dining spot offers a charming riverside view and a menu filled with gourmet dishes made from seasonal ingredients.
Diners frequently mention the impeccable service and the chef’s signature dishes. The restaurant offers a variety of hearty meals, from succulent steaks to exquisite seafood dishes.
Another fine dining gem is the Schoolhouse at Cannondale. Nestled in a historic schoolhouse, this restaurant combines rustic charm with a sophisticated menu.
People love the intimate setting and the creative dishes that change seasonally, ensuring each visit offers something new and exciting.
Engage in Outdoor Sports and Activities
Weston is not just about serene walks and food; it’s also a fantastic spot for outdoor sports enthusiasts. One of the most popular places is Bisceglie-Scribner Park, which has facilities for soccer, baseball, and basketball.
The park is a community favorite, providing ample space for children to play and adults to indulge in various sports.
For tennis lovers, the Weston Field Club offers excellent tennis courts. It’s a private club, but they offer trial memberships and special event invites to the public from time to time.
The club also has swimming pools and golf courses, making it a great all-in-one recreational spot.
Seasonal Activities and Events: Enjoying Weston Year-Round
Weston offers an array of seasonal activities that ensure there’s always something exciting going on. In the summer, Weston’s local parks often host outdoor movie nights, which are a hit among families and friends.
The Westport Farmers Market is another summer highlight. Located just a short drive from Weston, the market opens weekly and offers an incredible variety of fresh produce and artisan goods.
Fall in Weston means pumpkin patches and apple-picking. Silverman’s Farm, located nearby, is a beloved spot for families looking to pick their own produce, enjoy hayrides, and get a taste of farm life.
In winter, Weston’s community parks convert into winter wonderlands. Weston Middle School frequently sets up an ice-skating rink, providing a festive atmosphere for both kids and adults.
Spring brings the annual Garden Club Plant Sale, a popular event for gardening aficionados. It’s a great way to buy new plants and flowers to spruce up your garden while supporting local causes.
Experience Weston Through Its Local Events
Weston takes pride in its strong sense of community, which is evident through its numerous local events. The annual Weston Flea and Farmer’s Market is a massive hit. Held from spring through fall, the market features a wide range of stalls selling everything from fresh produce to antiques.
Locals cherish this gathering as it’s a fantastic way to meet neighbors and support local sellers while walking away with some unique finds.
Music lovers should not miss the Weston Family Fun Day, held each June. This event includes live music performances, food trucks, and games for children, making it a perfect family outing.
The town also hosts the Weston Arts Festival, a smaller but equally vibrant event that brings artists and art lovers together for a weekend of creativity and inspiration.
Weston’s Memorial Day Parade is another must-attend event. It brings the whole town together to honor the nation’s heroes, featuring marching bands, floats, and a touching ceremony at the cemetery.
Local Shopping Gems in Weston
For those who love to shop, Weston offers some fantastic local boutiques. The Weston Shopping Center is a hub for all your retail needs, featuring a variety of shops ranging from fashion to home goods.
A standout store in the area is The Pantry, which offers everything from gourmet foods to household essentials. It’s often praised for its high-quality goods and friendly service.
Westport, just a short drive away, offers extended shopping opportunities with its vibrant downtown area. Stores like Groove, offering trendy kids’ clothes, and Savvy & Grace, a boutique known for unique gifts and home décor, are well-loved by locals.
For the book lovers, Westport’s all-time favorite, the Westport Book Shop, offers a charming selection of new and used books. It’s a cozy spot to find your next great read.
Perfect Day Trips from Weston
If you’re looking to explore beyond Weston, there are several excellent day trips you can consider. One fantastic destination is the beautiful coastal area of Rhode Island, perfect for beach lovers and seafood enthusiasts.
The beaches here are well-maintained and offer a tranquil setting for relaxation. Alongside, you can also find some premier hotels for a sumptuous retreat if you wish to stay overnight.
For nature enthusiasts, a trip to the nearby Redding offers the opportunity to explore the hiking trails of the Devil’s Den Preserve, further extending your outdoor adventures.
Rhode Island is also home to some leading coffee houses where you can enjoy a delightful cup of joe while exploring new locales.
Another thrilling option is to visit the unique and unexplored spots in Rhode Island, from hidden coastal retreats to historic landmarks that offer a blend of relaxation and learning.
Enjoying Weston’s Nightlife
While Weston is best known for its daytime activities, it doesn’t fall short on evening entertainment. For a relaxed evening, visit The Spotted Horse Tavern in nearby Westport. Known for its lively atmosphere, great food, and classic drinks, it’s a favorite hangout spot among locals.
The Playhouse Theater in Westport is another evening gem. It frequently showcases plays, adding a cultural touch to your evening spectacles.
If you’re into live music, check out the music scene at The Ridgefield Playhouse, which offers concerts and comedy shows all year round.
For a quieter evening, the Weston Library frequently organizes book readings and discussions which can make for an intellectual and serene night out.
Staying Active with Community Classes
Weston offers a variety of community classes ranging from fitness to arts and crafts. The Weston Parks and Recreation Department offers numerous courses for all age groups.
You can enroll in yoga sessions, painting classes, or even cooking workshops. Local residents find these classes a great way to stay active and meet like-minded individuals.
The Weston Public Library also offers tech classes, language workshops, and book clubs, making sure there’s something for everyone.
If you are a fan of holistic health, consider attending one of the leading yoga retreats in nearby Rhode Island. They offer a fantastic way to unwind and reconnect with yourself.
These classes and workshops are periodically posted on the town’s official website, so be sure to check for updates regularly.
Discover Hidden Gems in Weston
While Weston may be a small town, it is packed with hidden gems that are waiting to be discovered. One such treasure is the Weston Flea and Farmer’s Market run by locals.
Held every Saturday from spring through fall, this market offers a variety of handmade crafts, fresh produce, and unique antiques. Locals love it for its community vibe and the one-of-a-kind items you can find there.
Another often overlooked spot is the Weston Historical Society’s secret garden. Tucked away behind the main museum building, this tranquil garden features native plants and flowers and is a peaceful spot for reflection or reading.
You might also want to explore the Lachat Town Farm, not just for its farm-to-table dinners, but for its enchanting gardens and outdoor workshops. It’s a great place for both families and individuals to enjoy nature and learn something new.
Getting Around Weston
Weston is a small, walkable town, but having a car can make it easier to explore all the nooks and crannies. If you don’t have a car, don’t worry; there are several ways to get around town.
Weston is serviced by a reliable taxi service that can take you around town or to nearby attractions. Uber and Lyft are also available, offering convenient rides at the tap of a button.
If you prefer a more eco-friendly option, consider renting a bike. Several local shops offer bike rentals, which is a fun and healthy way to explore Weston and its scenic trails.
For those visiting from out of town, the nearest major train station is in Westport. From there, a short taxi or bus ride will bring you into the heart of Weston.
When to Visit Weston
Choosing the right time to visit Weston can greatly enhance your experience. Each season has its own unique charm, so here are a few tips on what to expect year-round.
Spring is a lovely time to visit. The weather is mild, flowers are in full bloom, and many of the town’s outdoor activities and events begin to kick off.
Summer is perfect for enjoying Weston’s parks, outdoor festivals, and nature preserve trails. The town buzzes with activity, and there’s always something to do.
Fall offers breathtaking foliage and is a great time for hiking and exploring local farms. Weston’s autumn scenery is a must-see.
Winter brings a quiet charm to the town. If you’re a fan of winter sports, you’ll enjoy ice-skating and the cozy holiday atmosphere that permeates the town.
Local Hotels and Accommodation
While Weston is a smaller town with limited accommodation options, there are several great places to stay nearby that provide excellent comfort and convenience.
One highly recommended spot is the Westport Inn, located just a short drive from Weston. This boutique hotel offers stylish rooms, a friendly atmosphere, and great amenities.
If you’re looking for a more luxurious option, the Delamar Southport offers an upscale experience with elegant rooms, a full-service spa, and fine dining.
Locally-owned bed and breakfasts are also a wonderful option. The Roger Sherman Inn in New Canaan provides a charming, historic setting with personalized service.
For a unique and rustic experience, consider staying at a local farmhouse. Many farms in the area offer guest rooms where you can enjoy a farm stay experience.
Local Tips for Visiting Weston
Get the most out of your visit to Weston by following these local tips. These insider secrets will help you blend in with the locals and discover the best of what the town has to offer.
First and foremost, take the time to talk to local residents. Weston is known for its friendly community, and locals are often more than willing to share their favorite spots or give you recommendations for your visit.
Another is to plan your visit around local events and festivals. This way, you’ll get a taste of the town’s vibrant cultural life and have a chance to participate in community activities.
While you’re in town, make sure to sample Weston’s local cuisine. Don’t just stick to the well-known spots; ask around for lesser-known eateries that might offer a more authentic dining experience.
Lastly, consider booking a guided tour if you’re interested in learning more about Weston’s rich history and natural beauty. Many local experts offer tours that provide deeper insights into what makes this town unique.
Local Businesses That Make a Difference
Weston has a variety of local businesses that not only provide great services and products but also give back to the community. These businesses enhance the local economy while making Weston a better place to live.
One such business is the aforementioned Weston Provisions. Beyond offering delicious, locally sourced food, they frequently participate in community events and charities.
Adam Broderick Salon & Spa is another local business that stands out. Known for their excellent service, they also support local arts and education initiatives, proving to be a valuable community member.
Lachat Town Farm, in addition to its role as a farm-to-table dining venue, organizes many educational programs and events for children and adults, encouraging sustainable living and farming practices.
These businesses are more than just places to shop or eat; they embody the community spirit that makes Weston such a delightful place to visit or live.
Day Trips: Expanding Your Adventure
If you’re looking to extend your stay and explore beyond Weston, there are plenty of exciting day trip options within a short drive. One of the most popular destinations is the thriving city of Norwalk.
Norwalk offers a mix of cultural, historical, and natural attractions. Visit the Maritime Aquarium for a fun and educational experience, or take a stroll through the SoNo Historic District, which is filled with unique shops and restaurants.
If you’re a fan of seaside charm, head to the coastal town of Mystic. Mystic Seaport Museum offers a fascinating look at maritime history, while Olde Mistick Village is a quaint shopping area with unique stores and restaurants.
For those interested in history, a visit to the historic town of Litchfield is highly recommended. Known for its beautiful colonial architecture and charming town center, Litchfield is a picturesque escape.
These day trips offer a fantastic way to experience more of what Connecticut has to offer, ensuring that your visit is both diverse and memorable.
Weston’s Best Kept Secrets
Weston has its secrets and lesser-known attractions that deserve the spotlight. One such hidden gem is the Alfred Brush Ford Hall. This stunning venue hosts a variety of cultural events, from concerts to lecture series.
Another secret spot is Devil’s Den Preserve’s hidden waterfalls. While the main trails are well-traveled, there are secluded areas where you can find beautiful cascading waterfalls surrounded by lush greenery.
Weston’s Enviroment Education Center is a quieter destination. This small, unassuming building offers educational programs and nature exhibits that are particularly engaging for kids.
For a touch of local history, check out the Aspetuck Valley Orchard. Not only can you pick fresh apples and berries, but you can also learn about the history of farming in the region while enjoying some delicious homemade cider.
These hidden treasures showcase the depth and richness of experiences that Weston has to offer, making it a town that’s well worth exploring.
Connect with Weston’s Vibrant Community
One of the best aspects of Weston is its strong, connected community. Getting involved in local activities is a great way to experience this first-hand.
Join a local club or organization. There are many options ranging from gardening clubs to book groups, providing an excellent way to meet new people and share common interests.
Attend town meetings and events. This not only keeps you informed about what’s happening in Weston but also allows you to become an active participant in the community’s future.
If you’re an outdoor enthusiast, consider volunteering for trail maintenance at Devil’s Den Preserve. It’s a rewarding way to give back while enjoying the beautiful scenery.
Weston’s volunteer fire department also welcomes community involvement. Participating in their events and fundraisers is a fantastic way to support local heroes while building community spirit.
Unforgettable Experiences Await
In conclusion, Weston Connecticut might be small, but it’s filled with unforgettable experiences and activities. Whether you’re hiking through Devil’s Den Preserve, enjoying a farm-to-table dinner, or exploring the hidden gems, there’s something for everyone.
With its vibrant community, rich history, and stunning natural beauty, Weston is a wonderful destination for visitors and a beloved home for its residents. Plan your visit today and discover all the magic that Weston has to offer.

Avery Ingram
Contributor