Known as the “City That Works”, Stamford is the second-largest city in Connecticut after Bridgeport. Nestled along Long Island Sound, just 35 miles northeast of New York City, Stamford offers visitors plenty of fun activities, attractions, shopping, entertainment, arts and culture, and dining options to enjoy.
Whether you’re planning a weekend trip or looking for a new place to call home, Stamford has something for everyone. From scenic parks and beaches to museums and theaters, this lively city provides year-round events, festivals and things to do for all interests and ages.
To help you make the most out of your time, here are the 12 top things to do in Stamford, CT:
Explore Downtown Stamford
As the economic and cultural heart of Fairfield County, downtown Stamford features beautiful architecture and offers premier shopping, dining and entertainment options. Take an afternoon to wander down Bedford Street, Atlantic Street and Main Street while checking out high-end boutiques, art galleries, cafes and restaurants.
Some of the top spots include The Avon Theatre, a historic movie palace, The Palace Theatre for concerts and comedy shows, and restaurants like Barcelona Wine Bar and Fortina. Don’t miss events like Alive@Five and Discover Downtown Stamford to fully experience this vibrant downtown.
Spend a Day at Cummings Park
Cummings Park is Stamford’s largest public shorefront park located on 24 acres along the West Branch of Stamford Harbor. It’s one of the best places in the city for outdoor recreation andrelaxation.
Go for a jog or bike ride on the 3/4 mile loop trail encircling the park while taking in views of the water and surrounding landscape. Pack a picnic to enjoy at one of the scenic lookout points or pavilions. Kids will love the creative playgrounds designed as ships and submarines.
In the summer, cool off by the Olympic-sized public pool or at the beach. Rent kayaks, canoes, paddleboards or rowboats and spend the afternoon on the water. With free admission and so much to do, you’ll want to dedicate a whole day here.
Step Back in Time at the Stamford Museum & Nature Center
For over 90 years, the Stamford Museum & Nature Center has been preserving Stamford’s rural agricultural past along with regional history, art, and natural sciences. Spanning 118 acres, it encompasses trails, gardens, a working farm, observatory, planetarium, and Heckscher Farmhouse from 1785 preserved with period furnishings.
Guests can feed and pet farm animals in the Bendel Family Petting Farm, meet raptors in the Birds of Prey program, and explore themes like maple sugaring and native American life through interactive exhibits and demonstrations. The on-site restaurant The Sweet Pea uses fresh ingredients right from the farm. With so much to discover, you’ll learn something new with every visit.
Tour Shippan Point
Get a taste of Stamford’s history with a driving tour through Shippan Point. As one of Stamford’s most affluent neighborhoods, this peninsula features waterfront estates, yacht clubs and beautiful scenery.
Cruise along Ocean Drive West and Shippan Avenue to admire the stately homes, boats in the marina and views across Long Island Sound towards Long Island. Photo stops along the way include Cove Island Park, where you’ll find picnic areas, a beach and the city’s only public boat launch.
Another highlight is Halloween Yacht Club, rumored to be an old speakeasy frequented by NYC mobsters. While access is private, you can still glimpse this Gilded Age building from the street.
Shop Until You Drop at Stamford Town Center
As Fairfield County’s largest shopping destination, Stamford Town Center features over 100 stores ranging from Macy’s and Saks Fifth Avenue to Banana Republic and Sephora. There is something for all tastes and budgets here.
In addition to retail therapy, this downtown complex offers plenty of dining options like The Cheesecake Factory, P.F. Chang’s and Shake Shack. Catch a movie at the Bow Tie Majestic 6 theater or be entertained at the Palace Theatre.
With so many stores, restaurants and things to do under one roof, you can easily spend an entire day -and find everything on your list- at Stamford Town Center.
Browse Art and Exhibitions at the Stamford Museum & Nature Center
Art and culture enthusiasts will enjoy exploring the Stamford Museum & Nature Center galleries showcasing rotating fine art exhibitions and works from New England artists. Mediums range from paintings to sculptures to textiles and photography.
Some fan favorites include massive LEGO sculptures depicting cities and landmarks, multimedia exhibits documenting local immigrant stories, and galleries highlighting Stamford’s history and landscape paintings of the surrounding region. Family programs allow kids to create their own masterpieces too.
Between thought-provoking installations, appreciated local talents, classes and its serene arboretum setting, the Stamford Museum & Nature Center appeals to art fans and creatives looking to find inspiration. Don’t miss the unique gift shop stocked with handcrafted jewelry, pottery and paintings to take a piece home with you.
Enjoy a Show at the Palace Theatre
For premier performing arts in Stamford, look no further than the Palace Theatre. This historic vaudeville theater-turned-cultural gem has been entertaining audiences since 1927 with live concerts, musicals, plays, standup comedy and children’s theater.
Recent top shows gracing the stage include Blue Man Group, Jersey Boys, Jim Gaffigan and How the Grinch Stole Christmas! The Musical. Even if you don’t catch a show, it’s worth stepping inside this renovated theater to admire the ornate architecture including brass railings, grand chandeliers and ceiling moldings.
With a diverse lineup of shows, reasonable ticket prices and prime downtown location, the Palace Theatre tops the list of performing arts venues in Stamford.
Go For a Hike at Mianus River State Park
Just 5 minutes north of downtown, the 707 acre Mianus River State Park provides a peaceful natural escape with hiking trails offering scenic river and forest views.
The portion of the Mianus River flowing through the park makes for a particularly pretty hike, especially in spring when 300-year old Mountain Laurel blooms. Well-marked trails range from easy 1-mile loops to more challenging 4-mile treks on the Mianus River Trail.
Outdoor enthusiasts will also enjoy fishing and snowshoeing in season. With picnic tables and playgrounds also available, Mianus River State Park appeals to families and nature-lovers alike seeking fresh air, exercise and natural beauty just beyond the city.
Tour Elegant Homes on the Holiday House Tour
For a glimpse behind the elegant facades of Shippan Point, attend the Holiday House Tour held the first Sunday of each December. Presented by the New Neighborhoods organization, this self-guided tour allows you inside exquisite waterfront homes dressed up for the holidays that are otherwise privately owned and not open to the public.
From charming cottages to grand oceanfront estates, these decorated holiday homes provide inspiration and delight. Tickets include access to all houses, bus transportation between properties, and a reception with live music and refreshments at the end.
It’s a wonderful opportunity to explore Shippan Point’s architecture and holiday cheer in style. Advance ticket purchase is required for this popular seasonal event.
Spend a Day at Cove Island Park
For swimming, boating, picnics and peaceful waterfront relaxation, head to Cove Island Park. Its scenic peninsula location in north Stamford jutting into Long Island Sound offers beautiful views across the water and plenty of recreational amenities.
Kids will enjoy the creative playground and popular nets climbing structure while adults can sunbathe on the sand beach, grill at picnic sites or launch kayaks and canoes from the public boat launch, the only one found in Stamford. Several hiking trails provide wildlife viewing opportunities in the park’s natural areas.
With lifeguarded swimming, a concession stand and walking paths connecting to Cummings Park, it’s easy to spend a full day enjoying everything Cove Island Park has to offer right on the Long Island Sound shoreline.
Climb Atop the Stamford Landmark Sign
No trip to Stamford is complete without a photo in front of the iconic Stamford landmark sign in Harbor Point. Installed in 2019 overlooking Stamford Harbor, this 12-foot tall sign illuminated with over 5,000 LED lights has fast become a popular spot for selfies and city skyline views.
The sign’s distinctive font mirrors “The City That Works” found on the city seal while evoking Stamford’s industries like finance, insurance, retail and technology.
While the sign reads “Stamford” from the front, the back is carved with phrases like “innovative”, “diverse” and “connect” reflecting core values of this thriving coastal city. It’s the perfect place to capture your Stamford visit memories.
Catch a Baseball Game at Harbor Yard Stadium
Nothing says summer like an evening at the ballpark, and the Stamford Harbour Yard Stadium is home to the Harbor Yard Smokies baseball team offering just that classic Americana experience.
Overlooking Stamford Harbor and Long Island Sound, this intimate waterfront stadium lets you catch fast-paced minor league baseball action while enjoying spectacular sunsets. Special events like Friday night fireworks and Sunday Family Fun Days make for an affordable and entertaining day or night out.
With players hoping to catch the eyes of Major League scouts, the baseball at Harbour Yard features talented up-and-comers and lots of exciting plays. No matter who wins, a Smokies game promises a fun, family-friendly summer activity.
Conclusion
From scenic parks and beaches to historic sites, attractions and entertainment, Stamford delivers small city charm combined with big city vibrancy and style. With this list of top things to do, you’ll be able to fully experience the best this coastal Connecticut city has to offer from culture and dining to recreation and nature. Whether planning a quick Stamford getaway or considering moving to this “City That Works”, you’ll find engaging, enriching activities for all interests year-round to fill your time.
So what are you waiting for? Start planning your visit to enjoy the best of Stamford, CT today!