30 of the most quirky & unique things to do in southern CT

sunset over the Connecticut shoreline in southern ConnecticutLooking for the most unique things to do in southern Connecticut?

 

The third smallest state in the USA, Connecticut packs more into its tiny borders than one might expect.

 

And much of the activity is within a short distance of the Connecticut shoreline.

 

Coastal Connecticut packs plenty of variety in its approximately 100 miles from Greenwich to Stonington. In different parts of southern Connecticut, you’ll find activities associated with:

  • Lifestyles of the rich and famous
  • Nautical lifestyles
  • Intellectual life in the middle
  • Historic attractions centered around one of the oldest settlements on the CT shoreline

Unique things to do in Southern Connecticut

Ready to start your tour of the most unique attractions, activities, and things to do in southern CT?

 

Then read on.

 

But first, a personal story.

Quirky things to do in Southern CT during Covid lockdown

I came to appreciate Connecticut as an adult.

 

But I appreciated the various things to do here even more during the Covid pandemic, especially the lockdown.

 

As the most populous part of Connecticut, much of Fairfield County was shut-down for months. If something wasn’t closed, like Greenwich parks, it was swamped with other people who had suddenly discovered the outdoors.

 

But the silver lining of having your normal routine adjusted by a pandemic was needing to get creative and do more research.

 

Some of the spots I discovered during the Covid lockdown have become my favorite things to do here.

 

Much of this guide to southern Connecticut started with the research and exploration of the state I had to do to keep my spirits up when we were all feeling the most isolated.

16 of the most unique things to do in southern Connecticut

Of the lengthy list of southern CT activities, what are the most unique?

 

As in, what are ones you would have a hard time experiencing somewhere else?

 

Stretching from Greenwich in the west to Stonington in the east, below are our picks for the most unique things to do in southern Connecticut.

1. Greenwich Polo Club

Polo player playing a game of poloWhile other places make a to-do about horse racing, no one enjoys the Sport of Kings quite like Greenwich.

 

The Greenwich Polo Club hosts matches on Sundays. These are as delightful affairs as those much better known horse-focused sporting events.

 

You’ll likely bump into a celebrity or two while taking part in the time-honored tradition of stomping divots in the field. The experience certainly makes for one of the most unique date ideas in Connecticut.

 

Prince Harry has played a match here, and many more of the rich and famous have enjoyed an afternoon picnic during a match.

 

As befits an unstuffy yet luxurious affair, be sure to bring a picnic of at minimum a bottle of champagne and cheese spread.

 

And definitely a polo shirt.

2. Merritt Parkway

This 37-mile parkway through the backwoods of southern Connecticut is a historic gem.

 

The Merritt Parkway was built before I-95 to help lower traffic volumes on the Post Road. My mother has memories of her parents going for relaxed Sunday drives on the Merritt Parkway, stopping to picnic on a shoulder along the way.

 

Today, it’s quite a bit more crowded. And yet trucks and commercial vehicles are banned due to the low height of the historic bridges crossing the parkway.

 

The bridges themselves are a draw. Each one was individually designed to represent architectural styles popular in the 1930s:

  • Rustic
  • Gothic
  • Neoclassical
  • French Renaissance
  • Art Moderne
  • Art Deco

The Merritt Parkway is also the site of the nation’s first clover leaf entrance and exit ramps. And the service areas were recently renovated for drivers needing a Dunkin’ Donuts fix.

 

Bring your hiking boots on your trip, if you’re so inclined. Some of the best hiking trails in Connecticut are scattered along the route of the Merritt.

 

Shortly before the Parkway ends after crossing the Housatonic River, you’ll find a small museum in Stratford devoted to the design and construction of this bucolic holdever through Fairfield County.

3. The Glass House

Philip Johnson's Glass House in New Canaan, CTPhilip Johnson was an American architect born in Ohio who settled in New Canaan, Connecticut. While his stature has diminished of late, he is considered one of the most influential 20th century architects.

 

Mr Johnson designed Abby Aldrich Rockefeller Sculpture Garden at the Museum of Modern Art and the former Four Seasons restaurant.

 

And one of the most famous of his works is only a 25-minute drive from downtown Greenwich, in New Canaan.

Design of The Glass House

Built over 37 years on 49 acres, Philip Johnson turned homebuilding on its head with The Glass House. Instead of dividing a single interior into rooms, he divided the space into 14 structures, each with a different function, for example:

  • Johnson entertained and enjoyed the views of the surrounding landscape at the Pavilion in the Pond
  • He called his warm weather retreat with both air conditioning and a television Grainger
  • Johnson read and slept in the Brick House
  • And used the Stucco Studio as a workplace and library

One of the most famous quirks of the house is that almost the entire structure is one room. Only the bathroom features enclosed and opaque walls.

 

Otherwise, the home is around 2,000 feet of open space with only floor-to-ceiling glass and the steel to hold the panels in place around the entire exterior. Johnson famously joked that he had the most beautiful and expensive wallpaper the world had ever known.

 

Johnson completed his home in 1949. He also designed such quirks as a brick guesthouse with no windows, an edgeless gatehouse called “Da Monsta”, and an underground art gallery styled after Agamemnon’s tomb.

 

He famously quipped that Architecture is the art of how to waste a space.

 

And perhaps he was thinking of the Glass House when he made that comment. While Johnson lived here for parts of his life, it eventually became just a space for entertaining.

 

After all, floor-to-ceiling glass doesn’t afford much privacy.

 

It’s now a certified National Trust Historic Site, open May 1 to November 30.

4. Sheffield Island Lighthouse

Sheffield Island lighthouse, a clambake here is one of the most unique things to do in southern ConnecticutFrom the bustling downtown of South Norwalk, ride the ferry from May to September out to Sheffield Island.

 

The island offers beaches, beautiful views of Norwalk harbor, waterside trails through the island’s wildlife refuge, and ample space for picnicking.

 

But the main draw is the Sheffield Island Lighthouse. Built in 1868, the lighthouse was in operation until 1902. Today, you can enjoy a tour of this historic site, and see sweeping views of Long Island Sound, and even the NYC skyline on a clear day.

 

But there are historic lighthouses up and down the East Coast, right?

 

There’s something more that’s unique to the area that happens here every Thursday evening from June to September.

5. Sheffield Island Clambake

One of the most unique and well-known displays of New England cuisine is the clambake.

 

A clambake is a traditional, New England, method of cooking seafood using seaweed to steam the quahogs, clams, lobsters, mussels, et cetera.

 

Order tickets for the Thursday evening clambake to enjoy:

  • A roundtrip on the ferry to Sheffield Island
  • Tour of the lighthouse museum

But the main attraction is the clambake, of course. A multi-course meal featuring corn on the cob, potatoes, clams, salad, and dessert are all served under a tented pavilion on the lighthouse lawn.

 

Be sure to bring your own beverages (including beer or wine), and plenty of bug spray.

6. Weir Farm

Nestled off the beaten path in Wilton, Connecticut, sits one of only two national historic sites devoted to the visual arts.

 

In 1882, Impressionist painter J. Alden Weir, established himself, his work, and his family at Weir Farm. Three generations of painters would follow until the site became a national historic site in 2005.

 

Visitors can explore the hiking trails through the former fields of the farm, take a tour of the Weir studio and home, and even paint their own masterpiece.

 

With the grounds of Weir Farm open year-round, it’s one of the best free things to do in Connecticut.

7. P.T. Barnum Museum

P.T. Barnum of circus fame was born in Bethel, Connecticut, but loved Bridgeport.

 

It’s where he spent much of his life, and even served as its mayor for a time.

 

And when he died and was buried there, he bequeathed much of his most unique treasures to the city.

 

In downtown Bridgeport, close to I-95, sits a unique red and yellow domed building made of stone and terracotta. Barnum designed the three-story building himself, intending it to be an institute for science and history.

 

Some of the oddities of the P. T. Barnum Museum’s collection includes:

  • A 1,000 square foot miniature circus
  • A replica of his original Fiji mermaid
  • A real unwrapped mummy named Pa-lb
  • A preserved elephant

After suffering some severe damage from a recent hurricane, the main building is closed, though some of the museum’s items are on display next door.

8. Yale University

The stacks at Beinecke, one of the most unique things to do in southern CTOne of the oldest universities in America sits in downtown New Haven, Connecticut.

 

But there’s plenty of things to do here, even if you’re not an alum.

 

Visitors to Yale University can walk the campus grounds, whose Gothic style, inspired by Cambridge and Oxford universities, are reminiscent of Hogwarts to some modern visitors.

 

Visit the world-class (and many of them free) museums on campus. Some of the most popular Yale museums include:

  • Yale University Art Gallery
  • Beinecke Rare Book and Manuscript Library
  • Yale Peabody Museum of Natural History
  • Yale Center for British Art

Afterwards, be sure to take the free daily tour of campus led by current Yale students.

9. Ivoryton Playhouse

As far as historic attractions focused on the performing arts goes, much of the attention goes to the Goodspeed Opera House.

 

But the smaller, unassuming Ivoryton Playhouse is just as unique, and with an interesting cultural history.

 

Built in 1911, this theatre is the oldest continuously performing summer theatre in the United States. And it’s been self-supporting for the entirety of its history.

 

A few of the famous names that have made appearances at Ivoryton Playhouse include:

  • Tallulah Bankhead
  • Groucho Marx
  • Marlon Brando
  • Katharine Hepburn

In non-pandemic periods, the troupe produces award winning comedies, dramas, and musicals throughout the year.

10. Essex Steam Train & Riverboat

steam trainConnecticut is all about quaint and appreciating the history of the state.

 

And one of the most quaint and historical experiences is riding along the Connecticut River by train and boat.

 

The only remaining steam train and riverboat connection in America is based in Essex, Connecticut, as the name implies. Navigators meet at the historic 1892 Essex train station to start their excursion.

 

Then, spend 2 and a half hours on a narrated trip up the Connecticut River Valley, seeing such sights along the way as Gillette Castle and the Goodspeed Opera House.

 

Visitors can add extra activities to their trip with the Essex Steam Train, such as a dinner train service, or hiking excursion to Gillette Castle.

 

Any time of year can be an appealing time to take this trip, as the 30 miles or so of the river from the mouth up to Middletown is picturesque villages and marshes. It’s why The Nature Conservancy deemed the Connecticut River Valley one of “the last great places on Earth”.

11. Gillette Castle

Gillette Castle in East Haddam, CT, one of the most quirky attractions in southern CTHaving explored much of Connecticut, another category of attraction that stands out is quirky eccentricities created by excess wealth.

 

An early 19th century example of that eccentricity is Gillette Castle.

 

William Hooker Gillette is best known for his portrayal of Sherlock Holmes. The original actor of this character introduced such iconic props as:

  • The bent briar pipe
  • Violin
  • Magnifying glass

He was even the source of the phrase, “Elementary, my dear Watson.”

 

But his 1919 home is an attribute to a rather odd gentleman. The 24-room mansion looks like a medieval stronghold from the outside, but the eccentricities certainly don’t stop there.

 

Some of the oddities that Gillette designed himself include:

  • A system of hidden mirrors for spying on public rooms from the master bedroom
  • Strange door knobs, locks, and light switches
  • A steam engine and railroad tracks that once circumnavigated the property
  • Walking trails featuring wooden trestles and arched bridges

Start your visit with a grand entrance by taking the Hadlyme ferry across the Connecticut River from Chester. From spring to fall, you’ll be sure to enjoy the beautiful views on your approach to the castle and state park.

12. Mashantucket Pequot Museum & Research Center

Revenue from the Indian Casinos like Foxwoods Resort Casino has funded some amazing institutions.

 

One of which is the Mashantucket Pequot Museum & Research Center, the largest Native American museum in the world.

 

This museum is a tribally owned complex documenting Native American and the natural history of Southern New England. The impressive collection is nestled in an ancient cedar forest close to Foxwoods.

 

The museum uses text panels, films, and interactive computer programs to educate on Mashantucket Pequot life through the ages.

 

But the coolest exhibits are the life-size dioramas.

 

Visitors start their visit in a simulation of a glacial crevasse in the last Ice Age. There, they can watch a simulated hunt by the ancestors of the Mashantucket Pequots, complete with the sound of creaking ice and winds.

 

Follow the path into a completely recreated 16th century coastal Pequot village to get a life-size view of life before the arrival of Europeans.

 

The learning experience continues with more exhibits about life from 1675 until the 1970s.

 

But nothing else compares to those expansive dioramas, in this writer’s opinion.

13. The Submarine Force Museum

Connecticut was the home of America’s nuclear submarine production.

 

And this Cold War holdover still has a presence in Groton, Connecticut at the Submarine Force Museum.

 

Head to the only museum in existence managed by the United States Navy to explore the world’s first nuclear-powered submarine.

 

Other items in the museum’s collection highlight the history of submarines from inventor David Bushnell, a Connecticut native, and his Turtle, constructed in 1776.

14. Connecticut’s Severed Arm of Saint Edmund

While Mystic, Connecticut, is itself an attraction, one of the lesser-known things to do in the area is certainly one of the most unique points of interest in the entire state.

 

Possibly the country.

 

Sitting off the coast of Connecticut, accessible by a causeway, sits Enders Island.

 

Originally a private estate, the Society of St Edmund, a group of monks, now own and occupy it.

 

This order started in France, but fled to the United Kingdom in the 19th century before settling on Enders Island, always traveling with their religious relic.

 

Today, that macabre relic is viewable in the chapel on the island: the severed arm of St Edmund.

 

Make the trek to see this Gothic holdover, and recreate your own medieval pilgrimage.

 

The island is lovely, too, and worthy of its own pilgrimage for an afternoon.

 

6 fantastically unique restaurants in southern CT

Southern Connecticut offers a culinary tour of historic and futuristic firsts.

1. Connecticut’s Classic Hot Lobster Rolls

The battle line of lobster roll devotees fluctuates, but there are two schools of thought for what a real lobster roll is: Maine and Connecticut.

 

And it’s largely a difference between mayonnaise and butter.

 

A Maine lobster roll is lobster meat tossed with mayonnaise in a buttered and toasted hot dog roll, served cold.

 

The Connecticut lobster roll, meanwhile, is hot lobster meat dressed with butter and served in a warm, toasted bun.

 

Doesn’t that sound way more delicious?!

 

The Connecticut lobster roll first appeared in the 1920s at a now-closed restaurant named Perry’s in Milford, Connecticut.

 

You can’t enjoy a Connecticut lobster roll in its birthplace, but it was such a hit here that this dish spread up and down the Connecticut coast.

 

Head to the Lobster Bin in downtown Greenwich for what is arguably the best lobster roll in Connecticut.

 

Some other southern Connecticut restaurants serving great lobster rolls include:

 

Save an appetite for the home of a heavy-hitting first in America, in New Haven, Connecticut.

2. Louis’ Lunch

Grilling hamburgers. How does eating a burger at their birthplace not sound like one of the most unique things to do in southern CT?!Many places claim to be the birthplace of the hamburger.

 

But the Library of Congress declared Louis’ Lunch in New Haven, Connecticut, the official cradle of this most American dish.

 

That said, they’re a bit stern in their requirements of enjoying a hamburger their way. Their stipulations include:

  • Cooking their burgers on the unique, vertical stove towers on which they’ve been using since 1898
  • Only using the condiments of cheese, tomato, and onions. Don’t bother asking for other condiments, as they simply don’t have them.

Louis’ Lunch was originally a lunch truck owned by the eponymous Louis Lassen. In 1900, a customer ran up and asked for a quick lunch to take with them.

 

Mr Lassen took trimmings from his more typical steak sandwiches, put it between two pieces of toast, and sold it to his customer.

 

Today, Louis’ Lunch has occupied the same location since the 1970s. They’re open for lunch and dinner, Tuesday through Saturday.

3. Miya’s Sushi

New Haven is home to a fantastic dining scene, beyond being the birthplace of the hamburger.

 

Pizza restaurants here frequently win national awards.

 

But one of the most interesting and unique restaurants in New Haven is the home of “future sushi”.

 

At least according to the current owner, Bun Lai Yoshiko.

 

Bun Lai’s mother, Japanese immigrant Yoshiko Lai, opened Miya’s Sushi in 1982. It holds the title for being the world’s first sustainable sushi restaurant.

 

Decades later, it remains a local favorite earning national recognition.

 

And Bun Lai has created an innovative menu serving local invasive species.

 

future sushi at miya's sushi in new haven, ctThe Future Sushi Voyage tasting menu offers an experience in Bun Lai’s vision of what the sushi experience may offer in 2150. While not your typical fare, be ready to try sashimi featuring such threats to native flora and fauna as:

  • Asian carp
  • Lionfish
  • Venison

That last one is native. But the white-tailed deer population has exploded in Connecticut without predatory species to keep them in check, wreaking havoc on native plant populations.

 

Many of these unique ingredients are often foraged by Bun Lai himself.

 

The menu may even include an insect or two, if you’re feeling particularly adventurous.

 

Be sure to wash it all down with such house-made infused sakes as watermelon chili.

4. The Place

If you’re looking for something truly unique to southern Connecticut, look no further than the seasonal restaurant, the Place.

 

Open May through October in Guilford, this entirely open-air camp kitchen cooks all its dishes over a fire pit since it opened in 1971.

 

The menu has simple and delicious local staples. Steak and chicken are options for the more squeamish, but the draws are the seafood:

  • Bluefish
  • Lobster
  • Shrimp
  • Roasted clams

The clams alone are a huge draw. The cooks put littleneck clams in the fire until they open, then douse them in a mixture of cocktail sauce and butter.

 

And everything is served on their firetruck red tables with tree stump seats.

 

Dining here is definitely a unique experience.

5. The Griswold Inn

While the classic American fare at the Griswold Inn is worth a visit, the most intriguing part about the Griswold Inn is its history.

 

The Griswold Inn is the among the oldest of America’s continuously-run taverns. This despite such historic hurdles as invading British troops (Essex is one of the only towns in America invaded by a foreign power) and Prohibition.

6. Mystic Pizza

This pizza place is most famous for the movie named after it.

 

Open since 1973 on the main drag of Mystic, Connecticut, all pizzas are made with a “secret sauce”, the recipe of which, just like in the movie, is a mystery to outsiders.

 

And just like in the movie starring Julie Roberts, the restaurant is strikingly similar to the one in the movie, though it wasn’t shot on location.

 

TV screens inside Mystic Pizza run the movie on a continuous loop, in case you need a refresher.

7 choices for southern Connecticut’s most unique shopping experience

During the Revolutionary War, Connecticut was known as the arsenal of America, as it was the most industrialized state in the Union.

 

New Britain was later the source for not only many manufactured goods in the 1800s, but also the machines and know-how to operate them.

 

And peddlers traveling the American frontier were stereotypically from Connecticut.

 

So of course Connecticut has some unique places for retail therapy.

1. Greenwich Avenue

What was once a muddy country road in a backwoods town is now one of the most cosmopolitan shopping districts in America.

 

The downtown Greenwich Avenue shopping district is a destination for all of Connecticut and beyond for the huge number of high-end luxury boutiques that line the street. It has still maintained its local offerings, as well, to keep what you’ll find here unique and interesting.

2. Antique shopping in Stamford, Connecticut

antiques on display in a shopThe City That Works, next door to Greenwich, hosts an entire antiques district for aficionados.

 

These are no flea market finds, however, you’ll find some of the best preserved antiques from any period for which you’re searching.

 

And you’ll pay top dollar for them.

 

Some of the top Stamford antique shops include:

Unique Southern Connecticut bookstores

With one of the earliest public school systems in the country, Connecticut has long had a high literacy rate.

 

So our small population has a high proportion of avid readers, and unique shops to serve them throughout southern Connecticut.

3. Diane’s Books

This cozy little shop is just off of Greenwich Avenue on Grigg Street in Greenwich.

 

Books are carefully and lovingly curated, with little descriptions and teasers hand-written above each book on sale.

 

Diane’s Books is worth perusing whenever you’re shopping Greenwich Avenue.

antique books4. Atticus Bookstore

A New Haven institution since 1976, the Atticus Bookstore on Chapel Street is a prime spot to rub shoulders with Yale students while grabbing a coffee and searching for an unexpected literary find.

5. R.J. Julia Booksellers

This bookstore on the main street of Madison, opened over two decades ago with a mission to be a place where writers meet readers. R. J. Julia Booksellers hosts over 200 events a year, hosting authors from around the country.

6. Book Barn

What began as a singular structure devoted to books has expanded to about half a million literary works, sprawled across five different buildings and even makeshift structures.

 

Book Barn in Niantic, Connecticut, requires some exploring, based on your personal literary interests:

  • Ellis Island sits at the entrance, with new arrivals waiting to be processed
  • Hades is a makeshift structure devoted to thrillers and romance novels
  • The Haunted at the back of the property hosts two stories of thrillers and mystery novels
  • The Annex hosts fiction, paperbacks, essays, and poetry
  • Last Page is home to nonfiction
  • The Main Barn is the final maze of books, especially more non-fiction

You’re guaranteed to get lost in here for hours, and you can even take breaks at the playground on-site.

7. Olde Mistick Village

Another Mystic contribution to the list of unique things to do in southern Connecticut, Olde Mistick Village is more than just a tourist trap.

 

ducks in the pond at olde mistick villageJust off of I-95, Olde Mistick Village is modeled after a New England colonial village, complete with such touches as:

  • Waterwheel
  • Duck ponds
  • A replica of a steepled New England meetinghouse
  • Victorian gazebo

The brick pathways connect the more than 40 shops sprinkled throughout the area, selling gifts from around the world.

 

And the quaintness gets kicked up a notch around Christmas time, when the Christmas shop on-site likely makes the vast majority of its sales.

 

That said, Olde Mistick Village hosts musicians, dancers, storytellers, and more events in the gazebo and meetinghouse throughout the year.

3 of the most unique events in southern CT

Sure, everywhere has a pumpkin festival, an arts and crafts festival, and the like, but where else on this continent can you burn an effigy of a public figure?!

 

That isn’t Burning Man, anyway.

 

Explore southern Connecticut for some of the best events distinctive to our corner of New England.

1. Shakespeare on the Sound

The cute, affluent Norwalk neighborhood of Rowayton hosts an annual tradition that locals love.

 

Shakespeare on the Sound hosts 16 performances in the open-air of Pinkney Park in Rowayton for two weeks each summer.

 

While the goal of the production is to make Shakespeare accessible, that doesn’t mean they skimp on quality. In fact, the performers hail from:

  • NYU’s Tisch School of the Arts
  • Yale School of Drama
  • Even Broadway

Sound expensive? There’s a suggested donation ticket price, though it’s not required.

 

Bring a blanket and a picnic to stake your space and make an evening of it. It could very well be one of the most romantic things to do in the summertime in Connecticut.

 

But bring bug spray, just in case.

2. Chowdafest

man working at chowdafest, one of the events that made the list of most unique things to do in southern CTEach September, Westport, one of the most charming towns in Connecticut, hosts a culinary event celebrating one of the most well-known New England fares: clam chowder.

 

Chowdafest happens annually in Sherwood Park. Guests can sample and judge more than 40 different chowder recipes from various restaurants.

 

Categories judged include Classic New England Clam Chowder and Most Creative Chowders.

3. Annual Burning of Benedict Arnold

Centuries later, New London, Connecticut, still really dislikes Benedict Arnold.

 

It’s hard to blame the city: Benedict Arnold was from nearby Norwich. But his story went sour after he turned traitor and fought for the British in the Revolutionary War. He slaughtered surrendering forces after capturing New London, then burned the city to the ground.

 

In fact, Arnold specifically ordered that “every building should be on fire.”

 

The people of New London never forgave him. To this day, locals hold such a grudge that Benedict Arnold’s name is used as a severe insult synonymous with traitor.

 

Locals also use it to imply an intended arson.

 

And starting just a year after the burning in 1782, the citizens of New London carried a two-faced effigy of Benedict Arnold before burning him. The tradition of parading and burning the traitor’s effigy continued until the Civil War, and restarted in the last decade.

 

The curious, or those who sincerely hate Benedict Arnold as well, can head to New London in September to witness the parade and burning. Check for the exact date each year before you go.

Discover even more unique, quirky, and distinctive things to do in southern CT

Want to keep planning your trip?

 

There’s plenty more unique things to do in southern Connecticut, I just got tired of writing.

 

Find even more interesting things going on in southern Connecticut on our list of free things to do in Connecticut. Plenty of the most interesting and unique attractions in southern Connecticut are also free, like viewing the mysterious and historic manuscripts of the Beinecke Rare Book and Manuscript Library.

 

Or checkout some of our other guides, like:

Whatever you do, and whenever you do it, we hope it helps you to re-find your love of Connecticut!