Like much of the state, most people only know Stamford, Connecticut, from passing through.
Even growing up in next-door Greenwich, CT, there weren’t many reasons to go to Stamford.
After all, being only 30 miles or so away from Manhattan, the City was always a bigger draw on weekends.
But the silver lining of the pandemic was a somewhat forced introduction to things to do in Stamford, Connecticut.
And there are a surprising number of options.
The city of Stamford feels like three very different entities ensconced within its borders:
- Coastal living meets wealth supplanting the industrial history of south of I-95
- The artistic and culinary scene in downtown Stamford
- A bucolic, New England small town feel in North Stamford
That diversity permits a personalized visit, regardless of the time of year you visit.
In fact, it may be why many companies on the Fortune 500 and Fortune 1000 headquarter in “The City That Works”. And also why the real estate market is through the roof here.
Ready to plan a trip to Stamford, Connecticut?
Then read on for our guide to the best attractions, activities, and things to do in Stamford, CT.
Things to do in Stamford, CT, during COVID
This writer spent a significant amount of time sequestered in Stamford during the heights of the COVID pandemic.
Especially in spring of 2020, Connecticut was even dissuading residents from leaving the state.
Greenwich and Stamford share a spit of land jutting into New York state. As such, we suddenly all found ourselves wedged into a peninsula between Long Island Sound and New York.
But necessity is the mother of invention. And finding unique things to do in Connecticut to keep ourselves interested was the initial source for this guide.
South of I-95
The above descriptor is not terribly sexy, but it’s easier to say than the cluster of neighborhoods.
Made-up of the Stamford neighborhoods:
- South End
The South of I-95 region of Stamford hosts extremes of coastal wealth and urban living.
Some neighborhoods, like Shippan, have long been associated with wealth. Others, like Waterside and South End, have lengthy industrial histories.
But thanks to the influx of companies in the financial sector, the area is rapidly gentrifying.
After all, this is one of the few strips of the Connecticut shoreline with relatively inexpensive real estate along the waterfront.
Some of the major draws to this region of Stamford include:
Perched along the water of Stamford’s harbor, Harbor Point is an ever-expanding section within South End.
Developers keep snapping-up portions of what used to be:
- Working class neighborhoods
- Old industrial yards
And throwing-up luxury condominiums.
But the businesses that have sprung-up to service the young urban professionals that work and live here make the results worth a visit.
This exclusive highrise neighborhood has its own:
- Restaurants, some overlooking the waterfront
Harbor Point Restaurants
A romantic evening stroll along the waterfront of Harbor Point down to Kosciuszko Park at the southern tip of the peninsula is a great start. Follow-up with a romantic restaurant with a view here and you’ve got a complete, unique, Connecticut date idea.
- Sign of the Whale is a popular bar with an outdoor patio
- Fortina serves decent pizza
- Mexican restaurant Mexicue is the only dining option in Harbor Point with water views
- Prime restaurant across the West Branch from Harbor Point has a lovely view as well
By far one of the most unique things to do in all Connecticut is here in this corner of Stamford.
Fans of antiques looking for something specific and well-preserved know to head to Stamford’s antique district.
These stores are not quaint shops, the kind you find upstate. Rather, they’re high-end stores in the industrial part of town boasting high-quality and high-priced antiques.
Some top antique shops in Stamford include:
- Hamptons Antique Galleries on Canal Street
- Avery & Dash Collections on Jefferson Street
- Stamford Modern on Pacific Street
Thanks to its proximity to the City, as locals call New York City, many NYC-based companies pick Stamford as their first point for expansion.
And so the city of Stamford gained Chelsea Piers in 2012.
Chelsea Piers features 465,000 square feet of space for the active.
Amenities at Chelsea Piers include:
- Athletic fields
- 65,000 square foot fitness center
- Skating rinks
- Baseball center
- Ballet school
- Batting cages
- Tennis and squash courts
- Volleyball and basketball courts
- An adventure center, with trampolines and rock walls
- Splash Zone with three water slides
- Three different-sized swimming pools
If you’d prefer to relax on your visit, Chelsea Piers also organizes classes for Pilates, yoga, and even massages.
Stamford, CT, Beaches
Stamford citizens don’t have to go far to enjoy some of the best beaches in Connecticut.
Cove Island Park is the largest beach in town, with over 80 acres of space to spread-out. But the largest is also the busiest.
Several of the other Stamford beaches are much quieter; perfect for a relaxing summer day.
As is the case with most beaches in this part of Connecticut, non-residents will need a parking pass to enter Stamford beaches in the summer months.
Separating the tony Shippan neighborhood from the rest of Stamford is Cummings Park.
This large park of 79 acres offers wide open spaces and sweeping views of Westcott Cove and Long Island Sound.
The park, boardwalk, and fishing pier offer a decent space for a waterfront stroll. More active types will enjoy playing basketball, softball, or tennis in the various recreational areas.
Boaters will also appreciate this park for its boat launch and marina.
And the snack stand in a building that looks like it belongs in South Florida will keep you sustained throughout your summer visit.
This park is even a draw in the winter months, with a hill that’s perfect for local sledding aficionados.
The city of Stamford named the park in honor of Homer Stile Cummings, who served as mayor of the city and later Attorney General under FDR. Mr Cummings used to take calm, relaxing walks along the beach to clear his head; something visitors can enjoy to this day.
Cove Island Park
For a fun day of outdoor recreation at one of the top parks in Stamford, Cove Island park offers a variety of activities:
- A one-mile loop of well-maintained walking and biking trails
- A children’s play area
- Expansive lawns for kite-flying
- Fishing along the rocky shoreline
- Birding along Holly Pond and Cove River (birders have recorded 287 species here)
- Summertime on-site restaurant
- A skating rink, open since 1973
But the main draw here are the two sandy beaches. A small bluff offers an excellent view of the Long Island Sound and is a great place to relax and take in the sights.
This 83-acre park also hosts:
- A marina
- Intertidal mudflats
- Salt marsh
- Views across to the coast of nextdoor Darien, Connecticut
Cove Island was originally a peninsula connected to the mainland by a thin strip of land to the north. Town residents in the 1600s used the area as a sort of pound to house stray livestock.
Residents who lost their livestock would have to pay a hefty fine of five shillings to get their animals back.
In the 1700s, a factory on the island manufactured bleached minerals, dye extracts, and liquorice. The factory burned in 1919, and the city converted the island to a park over the next few decades.
Continue past Cummings Park towards Shippan and you’ll come across West Beach.
This smaller, quieter beach is across Westcott Cove from Cummings Park.
West Beach has fewer amenities than the other parks, but the quiet is worth a visit.
That said, you’ll still find:
- A children’s playground close to the beach
- Lifeguards on duty at peak times in the summer months
If you develop an appetite while you’re here, head to one of the cafes, delis, and sandwich shops steps away from the beach on Shippan Avenue.
Top Things to do in Downtown Stamford, CT
The high rises clustered near the Stamford train station and I-95 is the section of Stamford most people recognize.
This is the center of town for enjoying the arts. And with 85 restaurants in its walkable, 16-block neighborhood, it’s also the center of Stamford’s dining scene.
And it’s a ten-minute drive from us in downtown Greenwich, which adds to the variety of options for our guests to enjoy while they’re visiting.
Some of the biggest attractions, activities and things to do in downtown Stamford include:
At the corner of Bedford Street and Broad Street, sits one of the largest public libraries in Connecticut.
And with its Ionic portico, it’s arguably one of the most attractive.
The front of the building dates to 1910, in a Georgian Revival style. Honorable John Day Ferguson, local lawyer and strong advocate of education and learning, left a large sum of money for building the library after his death.
Even visitors to Stamford can appreciate the coffee shop on-site, as well as the used bookstore.
Mill River Park
What was once a major eyesore on the edge of downtown is now one of the top attractions.
The Rippowam River forms the boundary between the West Side and downtown Stamford neighborhoods.
And until the city began a 6-year restoration project on the river starting in 2007, the banks of this river were a depressing place.
But Mill River Park opened in 2013, and is now a major asset to locals.
The biggest draw to the park is the David & Marian Nissen Carousel, with seats on 30 charming and handcrafted animals.
On the other side of Mill River Park is the Steven and Alexandra Cohen Fountain, with dancing streams of illuminated water. The fountain converts to a skating rink in the winter months.
Both banks feature undulating paths, winding through the gorgeous greenery. There are plenty of benches and spots to relax and enjoy the sound of running water.
And being able to sit in the middle of a city, listening to a babbling brook, is a remarkable experience in and of itself, to this writer.
Saint Andrew’s Episcopal Church
Nestled among the modern city is a throwback from the Victorian era.
Saint Andrew’s Episcopal Church is an Anglo-Catholic parish. It is inclusive and open to all, as a member of the glocal Anglican Communion and Episcopal Diocese of Connecticut.
Congregants consecrated the church in 1861, in a structure that New York architecture firm, Browne and Rogers, designed.
The church added the belltower at the front in 1930.
The grey stone church features a chancel, cloister containing the sacristy and parish office, and parish hall.
Gilded wooden fish embellish the red doors of the church. They’re a symbol of the church’s patron saint, Saint Andrew, who was a fisherman before becoming a fisher of men as an apostle.
Events, Movies, Theater, & Music in Stamford
Not every town plays host to acting troupes, filming studios, and independent movie theaters.
Even some cities aren’t so lucky.
And yet, Stamford is blessed with an abundance of entries from this list.
One downtown attraction, the Avon Theatre, is on the list of hidden gems in Stamford.
More on that later.
Stamford Center for the Arts
Centered on Atlantic Street in downtown Stamford is a major Connecticut institution.
The Stamford Center for the Arts stretches along a sizable section of Atlantic Street. Two separate buildings make-up the center:
- The Palace Theatre
- Rich Forum
The Palace Theatre
Constructed in 1927, The Palace Theatre is a draw to downtown Stamford simply for its Art Deco venue.
But of course, most people come for the live shows.
What began as a venue for vaudeville, The Palace Theatre was then a movie theatre from the 1940s until 1983. Since then, it’s been a live performance theatre that seats 1,580 of your closest friends.
This is the place to go in Stamford for a broad array of live performances, including:
- Comedy shows
- Magic shows
- Off-Broadway musicals
- Even Stamford Symphony Orchestra concerts
The Palace Theatre still uses its main stage, though some performances happen in the more personal UpStage. Performances in UpStage feel more like being in a small club, creating a more intimate experience.
A show at the Palace Theatre could be one of the most romantic things to do in Connecticut.
Four blocks away is the Rich Forum.
Some heavy-hitters in daytime television are filmed here:
- Jerry Springer
- The Steve Wilkos Show
Scoring tickets to the taping of one of these shows would certainly make your visit to Stamford unique.
Ask anyone who’s been to Curtain Call, and they’ll tell you that this community theater puts many a New York City stage to shame. The world class shows at Curtain Call are a fun and affordable way to experience Stamford and often top the list of best things to do in the area.
This non-profit hidden gem boasts:
- Two stages, the 184-seat Kewskin Theatre and 100-seat cabaret-style Dressing Room Theatre
- Year-round productions, with twelve or more shows a year
And a rich lineup of fantastic local talent.
Curtain Call even played a part in developing some of that local talent, with various courses on the theatrical arts.
Alive @ Five summer concert series in Columbus Park
Alive@Five has grown quickly in local memory from a two-bit Thursday afternoon event to a pretty big deal. It’s certainly one of the biggest events in Stamford, Connecticut, of the year.
Artists, which seem to get more and more famous with the passing years, come to perform Thursday evening at Columbus Park. The crowd can also enjoy food and drink specials from the local restaurants.
Stamford’s Thanksgiving Day parade
Winding its way through downtown Stamford, this is still an annual draw to Connecticut in November.
After all, the Stamford Thanksgiving Parade is not as big as New York City’s, but it also doesn’t have the huge crowds.
Favorite things to do in North Stamford, CT
Speaking of crowds, head north from downtown to find the much more bucolic area of town locals call North Stamford.
This is the area of the city that features a New England small town feel.
It’s easy to forget that you’re in one of the largest cities in Connecticut while exploring this part of town.
Especially when you’re enjoying the many opportunities for outdoor activities in this area.
Stamford Museum & Nature Center
The former summer home of department store founder, Henri Bendel, this 118-acre property is home to:
- A working farm
- Museum and gallery
- Interactive nature center
- Tons of outdoor trails
The main building features a mock Tudor style reminiscent of a common architectural style from the 1920s.
The half-timbered Bendel Mansion still occupies the site. You’ll also find a collection of marble statues in a hilltop garden overlooking Lake Laurel.
Chickens, sheep, goats, and horses stock the center’s Heckscher Farm, while the seasonal Maple Sugar House is a draw in the spring.
The Stamford Museum & Nature Center also offers exhibits and weekend festivals that showcase the natural history of New England. This destination is fun for the entire family.
Among the many various exhibitions on the grounds of the Stamford Museum & Nature Center is also an observatory.
This small facility was commissioned in 1967 at the height of the Cold War. The dome protects the Stamford Observatory’s 22-inch research telescope, there since its founding.
Public viewing sessions happen each Friday night at 8 and 10 PM. The observatory also hosts lectures and a collection of celestial items such as a meteorite found in Argentina.
Stamford Historical Society
Down the street from the Stamford Nature Center is the Stamford Historical Society.
This educational and research center collects, interprets and preserves material aspects of Stamford’s history since its founding in 1901.
And considering the lengthy history of Stamford, with a town charter first signed in 1640, there’s a lot to preserve.
Situated in the 1699 Hoyt Barnum House, this organization also hosts:
- Guided tours
- Specials events
Shakespeare On The Green
If you’re in Stamford in July, Curtain Call hosts an annual performance of a Shakespeare Play outdoors in North Stamford.
North Stamford is one of the few places to enjoy Shakespearean theatre under the pines; hosted at Sterling Farms.
Bring a picnic, and seating: beach chairs, blankets, or call in advance to reserve a spot.
While performances are free, the acting troupe encourages donations.
Hidden gems and top 10 things to do in Stamford, CT
To the untrained eye, there’s not a ton to explore in Stamford.
But there are a couple cool things to check-out, whether you’re a local, a new arrival, or just passing through.
1) Kosciuszko Park
In an area where the shorefront is at a premium, Kosciuszko Park is a gem.
The main draw to this 7-acre park, just south of Harbor Point, is the walking path that circles the park’s edge for almost a mile.
Much of the path offers gorgeous views of Stamford’s harbor and Long Island Sound.
Other amenities include:
- Baseball field
- Picnic area
- Play equipment
2) First Presbyterian Church
Nicknamed the “Fish Church” for its unusual shape, First Presbyterian Church was designed by architect Wallace K. Harrison. It is a breathtaking architectural landmark.
The skyscraping tower outside, called the Nestle Carillon, is home to 56 bells and is 260 feet tall.
But the inside of the church is amazing. Guests can admire an interior that is made of 20,000 pieces of glass in 86 different colors.
The church congregation chose the outline of the building and floor plan to evoke the fish symbol, so important to early Christianity. They consecrated the church in 1958.
The stained glass windows illustrate the crucifixion on the right side of the church, and the resurrection on the left.
The wooden cross in front of the pipe organ is clad with wood from Canterbury Cathedral.
Locals treat the grounds of the church as a park in the summer months, with plenty of people enjoying the green space well into the evening.
2) Ukrainian Museum and Library
The Ukrainian Museum and Library of Stamford is the oldest cultural institution established in North America by Ukrainians.
Without question, it is one of the most unique collections in Stamford.
This institution opened its doors in 1935, with two great rooms on the Quintard Estate.
In the 1980s, the collection expanded to two floors of the mansion, while the library and archives moved to the former St Basil Preparatory School.
The collection of arts, folk and religious art, and literature from the Ukrainian community continues to grow.
3) Goodbody Garden & Fort Stamford Park
Hidden away in a residential neighborhood off of Westover Road, this little park is a treat.
Goodbody Garden is a quiet botanical garden, offering a tranquil, restful, space. New York financier Marcus Goodbody landscaped in a formal style when this was his early 20th century home, with:
- Italianate balustrades
- A stone-pillared pergola
- Sunken garden
After falling into disrepair, the Stamford and Glenbrook Garden Clubs returned it to its former glory.
Spring and early summer is delightful here, especially when the peonies and magnolias are in bloom.
And yet, the real gem of this park is the ruins of old Fort Stamford, active from 1781 to 1783. While there are not many traces left, the 340-year old earthworks that remain from the Revolutionary War are unique to the area.
After General Washington took his troops south from New York, General David Waterbury built this fort to protect against British raids. With a clear view of Mianus River and Long Island Sound before the forests regrew, the strategic importance of the site makes sense.
4) Bedford Street
While all downtown Stamford didn’t survive the late 20th century onslaught of malls intact, a portion of its original central district escaped the wrecking ball.
Bedford Street, stretching from the Ferguson Library to Latham Park, is a line of restaurants, cafes, and boutiques.
Especially during warmer months, Bedford Street has a European atmosphere to it, with plenty of outdoor dining options.
Some personal favorites include:
5) The Avon Theatre
While every spot in America can boast one of those huge, multi-screen cineplexes with about as much character as your local McDonalds, not every area has its own film center.
The Avon Theatre offers big-ticket films as well as artistic independent films in a restored early 20th century movie theatre.
Dinner at one of the great restaurants nearby on Bedford Street before a movie here is one of those classic Connecticut date ideas.
6) Mianus River State Park
Much of the border between Stamford and Greenwich is swathed in green.
And the gorgeous and expansive Mianus River State Park protects much of it.
Multiple trails crisscross the lush green woods of this 400-acre park that straddles the 20-mile Mianus River.
The trails are mild to moderate in difficulty, and pass through varied terrain in the park, including:
- River bottomlands
- Mountain laurel forest
These trails are also one of the most dog friendly parks in Connecticut, though keep your friend leashed if he has a habit of getting lost in the excitement of chasing after wildlife.
You’ll find maps at each of the entrances. Be sure to take a picture on your phone.
Speaking from experience, it’s easy to get lost. And cellphone reception can get shoddy, depending on your carrier.
But getting lost and stumbling upon the ruins of an old farmhouse is half the fun!
Provided you don’t literally stumble upon it, at least.
If a visit appeals to you, head there early, before the two small parking lots, one accessible from each town, fill up.
7) Bartlett Arboretum
While not as expansive as Mianus River Park, Bartlett Arboretum is every bit as beautiful.
This greensward in North Stamford offers 93 acres of hiking trails, gardens, and wetlands.
Bartlett Arboretum and Gardens is clustered near the Stamford Museum & Nature Center and Stamford Historical Society.
So lumping the three together would make a full day.
Many of the flora in the collection are from New England. That said, you’ll find additions from all over the world, some planted as long ago as a century.
There’s no question it’s one of the best free things to do in Connecticut.
8) Philip Johnson Glass House
This is not officially in Stamford, but it’s so close, in nearby New Canaan, that it has to be on the list.
The Philip Johnson Glass House is an iconic example of modern architecture, and is one of the most unique attractions in Connecticut.
First designed in 1949 by the eponymous architect, the Glass House is a soaring demonstration of:
The only space not exposed to the outside world is the bathroom.
Head to the charming Connecticut town of New Canaan to find the Visitor’s Center. From there, you’ll ride a shuttle for a 3/4 mile guided tour of the estate and structures.
9) Best Restaurants & Hidden Gems in Stamford
Stamford hosts a vibrant dining scene. But a few restaurants are so unique and special, that they make this list of hidden gems:
- Lorca Cafe
This Spanish-inspired pastry & coffee shop on Bedford Street is perfect for some coffee & churros on a rainy day. You won’t be disappointed.
- Lakeside Diner
This diner has been serving since the late 1950s, and is best known for its cinnamon sugar donuts and lakefront view.
- Cafe Silvium
This casual, Italian, neighborhood trattoria in the Cove neighborhood doesn’t always get the praise it deserves.
An Albanian family has been running this pizza joint close to the Darien border for a long time. I found this place during the pandemic, and joined long lines of people for their square-cut pizza, serving take-out only.
- Sugar Bowl Luncheonette
This is another hidden spot. While it’s not in Stamford, it’s close-by on the main street of Darien, Connecticut. This diner is a throwback to the 1950s; and still serving great food at reasonable prices.
5 great hotels in Stamford, CT
Ready to plan a longer visit to the area?
As befits one of the largest cities in Connecticut, there are plenty of lodging options within city limits.
Some of the most popular Stamford, CT, hotels include:
Stamford Marriott Hotel & Spa
Courtyard by Marriott Stamford Downtown
The Lloyd, formerly known as Hotel Zero Degrees Stamford
As far as bed and breakfasts go, there are none in Stamford. But there is a bed and breakfast inn located in downtown Greenwich, Connecticut, right next door.
That is, us.
Getting to Stamford & When to Visit
As this writer mentioned before, Stamford juts into New York State.
As such, it’s easy to reach from New York City.
It’s an easy drive of about 40 miles from midtown Manhattan, via either:
- The Merritt Parkway, called the Hutchinson River Parkway in Westchester County, New York
If you prefer to take the train, trains leave from Grand Central Terminal on a regular basis.
During peak travel hours, express trains to and from NYC leave every few minutes.
When to visit Stamford, Connecticut
As is the case with the rest of Connecticut, when you visit depends on what you want to experience.
Summertime is perfect for enjoying a Connecticut beach vacation.
Fall in Connecticut is gorgeous. And the Greenwich-Stamford area is a perfect starting point for exploring the rest of Connecticut and New England.
Winter is perfect for exploring the arts scene in Stamford. And considering the excellence of the train system, our area is perfect for winter weekend getaways from NYC for couples by train.
Stamford, CT, Visitor’s Guide
Ready to keep exploring the Connecticut shoreline?
Then check-out our guides to attractions, activities, and things to do in Greenwich, Connecticut.
Our read our guide to the most unique, or eccentric, things to do in Connecticut.
We hope you re-discover your love of Connecticut!
Edited, updated, and republished on July 16, 2021