Things To Do In CT In May: Top 23 Most Unique Spots | Stanton House Inn
sailing the shoreline is a great choice for things to do in ct in may

Things to do in CT in May: Top 23 Most Unique Spots

ducklingsFinally! The snow is melting away, and the ice is thawed. The summer warmth is on the horizon like a much-needed finish line, and the prospect of you exiting hibernation from the winter is upon you.


It’s the perfect time for you to take a weekend getaway or a day trip to the gorgeous CT to breathe in some fresh air and sight-see outside the town you’ve been stuck in for months.


There are tons of modern activities along with historic sites, so there’s something for everyone.


Check out these 14 top-rated activities in CT in May to enjoy during your spring celebration!

The very best things to do in CT in May, statewide

No matter where you are in Connecticut, May is one of those months where the state really shines. Any direction you go makes for fantastic summer road trips.

Soak Up the Great Outdoors at a State Park


heublein tower in SimsburyConnecticut is home to one of the most stunning segments of the Appalachian Trails. 


Running from Salisbury to Kent, you can hike to Bear Mountain or head to Norfolk, CT, to discover Connecticut state parks like:

  • Dennis Hill State Park
  • Haystack Mountain State Park


Other fantastic Connecticut hiking trails here include:


If you’d rather take to the waters instead of hiking, the Housatonic River is ideal for outdoor activities involving kayaks and canoes. It’s all about taking your time to explore the meandering river valley and its breathtaking beauty.

Hit Up Local Gift Shops


You might be thinking, “What the heck will I even find at a gift shop?” Don’t worry! It’s not all just knick-knacks. Although, who doesn’t love a ceramic cat for a bookshelf?


At Connecticut gift shops, you’ll find lots of goodies for yourself or your loved ones. 


Does your aunt love tea? We have a shop for that! Does your dad love coffee? There’s a shop for that. Does your mom love to crochet? You can find a shop that has gorgeous blankets already made, or you can find a spot that has gorgeous yarn ready to be knitted. 


There are oddity shops, bookstores, clothing spots, flea markets, antique shops, accessory showrooms, and more.

Appreciate All the Connecticut Art Museums


Whether you’re trying to just kill an hour or spend the whole day in a museum, there are many gems of museums throughout Connecticut


Wadsworth Atheneum

wadsworth atheneum, one of the best things to do in ct in mayThis museum was my initial reason for visiting Hartford. Art collector Daniel Wadsworth started this public museum, the first of its kind in the US, in 1842.


Today, if this museum was located in New York City or Boston, it would likely be one of the most visited spots in the Northeast. But its relative isolation helps keep this under-the-radar wonder accessible.


With 50,000 items in its collection, be ready to not be able to appreciate everything in one visit.


The museum heavily focuses on 19th and 20th-century American artists, but the collection spans 5,000 years of art history.


Some of the major artistic draws include the museum’s collections of:

  • Hudson Valley School paintings
  • Art from the French Revolution period
  • Norman Rockwell
  • European and American Impressionist paintings


New Britain Museum of American Art


A fun fact is that the New Britain Museum of American Art was the first museum in the country devoted to displaying American art. It’s been doing so since 1903.


The Brant Foundation Art Study Center


The Brant Foundation Art Study Center is a one-of-a-kind gallery that lends works to more than a dozen exhibitions annually. 


It strives to promote education and appreciation for contemporary art and design. 


This center is every art lover’s dream destination!


Neuberger Museum of Art


While this may not officially be a museum in Greenwich, CT, it’s just over the border in Purchase, New York. The Neuberger Museum of Art is located on the SUNY Purchase campus and is an easy drive from downtown Greenwich.


Aldrich Contemporary Art Museum


For more art museums, be sure to visit the Aldrich Contemporary Art Museum. It’s the only museum in Connecticut devoted to displaying only contemporary art, and one of the best things to do in Ridgefield, CT.


Top things to do in CT in May in the western half of the state

From ritzy Greenwich to collegiate New Haven, this dense stretch of the Connecticut shoreline hosts a broad range of attractions.


Browse Through the Grounds of the Philip Johnson Glass House


Offset from the Glass House sits a guest house completely enclosed in brick. Philip Johnson named it, appropriately, the Brick House. It contains a bathroom, library, and single bedroom with a vaulted ceiling and shag carpet.


Later, Johnson added a painting gallery, followed by a sky-lit sculpture gallery.


The last structures Johnson built on the estate were a library and a red and black reception building. 


Johnson claimed that, together, his one-room buildings made a complete work of art: the Philip Johnson Glass House.


Be Amazed at the Yale University Art Gallery


yale university art galleryYale may not be the oldest university in America. Still, its premier art gallery is the oldest university art museum in America.


It’s also the oldest in the entire Western Hemisphere.


Established in 1832, the Yale University Art Gallery first occupied a Romanesque building on Chapel Street.


The art gallery rambles with multiple expansions on four floors thanks to an ever-expanding collection.


Some of the largest collections in terms of pieces include art from:

  • The ancient Mediterranean world (13,000 objects)
  • The African continent (2,000 objects)
  • The ancient Americas (1,500 objects)


While the collection spans human history, a sizable portion of the collection is devoted to:

  • African Sculpture
  • 1800s American Realism
  • French Impressionism
  • Early Italian Paintings


Modern art, two of the most famous pieces being Kazimir Malevich’s The Knifegrinder and Joseph Stella’s Brooklyn Bridge


As it befits an American institution, American art has a significant presence. There are even exhibits devoted to decorative furniture and arts from America, especially New England. This museum needs to be on the top of your bucket list!



See All of 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
  • Planetarium
  • Observatory
  • Playground
  • Tons of outdoor trails


stamford museum and nature centerThe 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 one of the best places to visit in CT 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.


The very best things to do in eastern CT in May

There’s so much more to eastern Connecticut than Mystic.


Though the attractions in Mystic, CT, are worth a visit in May, to be fair.


A few options from the extensive menu includes:

Stroll Along the Connecticut River


Expansive and stunning, the Connecticut River is a beautiful starting activity after you enter the state. 


Breathe in its fresh air, take in the sight of birds overhead, and relax to the sound of the gentle waves. 


You can use this as a hiking opportunity, or you can grab a blanket and relax next to the water with a book and some snacks.

Feel Like Royalty at Gillette Castle


gillette castle, one of the best things to do in ct in mayHaving 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


William Gillette 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 to one of the best state parks in CT 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.


Win Big at Mohegan Sun Casino


mohegan sun casinoGamblers from all over the United States head over to Connecticut to test their luck. The most popular casino in the state is Mohegan Sun in the town of Uncasville, CT


It’s a resort known for gambling, entertainment, and endless activities. 


Mohegan Sun Casino is the perfect spot to spend the whole day if the outside world is raining buckets and you’re still looking to do some exploring!



Don’t Miss Out on Mystic Museum of Art


On the edge of downtown Mystic, overlooking the Mystic River, the Mystic Museum of Art is rapidly developing into an attraction in its own right. 


While this charming art gallery is petite, the art exhibitions change every few months. They are displayed in a gorgeous space adorned with plenty of natural light.


The surrounding manicured gardens are also lovely. Besides, entrance is free, so your time is the only cost of a visit. An artist colony started the Mystic Museum of Art in 1913. Visitors can participate in one-day art workshops or children’s art classes.

Dive into Marine Life at Mystic Aquarium


penguin at mystic aquarium, one of the best things to do in ct in mayNot into learning the history of mankind’s efforts to exterminate what’s left of the world’s megafauna at Mystic Seaport?


Then head to the second major attraction built in the Mystic area to keep you occupied: Mystic Aquarium.


This attraction even hosts living whales of the beluga variety.


Many of the exhibitions are outside, including the belugas and other creatures:

  • Seals
  • Sea lions
  • Penguins
  • The aviary known as Boomerang Island


But a visitor could knock all of these off their list in about 30 minutes if the weather is uncooperative.


Inside exhibits include more of the typical aquarium fare:

  • Fish
  • Jellyfish
  • Sharks
  • Stingrays


While this aquarium is fairly small, it is heavily involved in researching, preserving, and protecting the life of our oceans.


So, there’s no guilt in supporting their mission.


This is the first attraction (of many) on this list that’s also one of the top indoor activities in Connecticut.



Spend a Day in Litchfield Hills


New Preston, in the Litchfield HillsHere in Litchfield Hills, you’ll discover a rich experience with top-tier dining, eclectic shopping, and more nature than you’ll ever hope to find close to New York City.


The Litchfield Hills embody New England charm, making it the ideal area to spend a day, a weekend, or a night out in the smaller town.


As far as New England road trips go, the scenery and understated beauty of Litchfield Hills are one of Connecticut’s best-kept secrets. It makes for one of the best road trips from New York City, anytime of year.


May is an ideal time to explore the attractions, activities, and things to do in Kent or any of the other small towns up that way.


What to do around Hartford, Connecticut, on a lovely May day

The state capitol has plenty to do, especially when the flowers are in bloom.


From the Elizabeth Park rose garden to downtown museums, you’re sure to find plenty to do on a gorgeous (or not so beautiful) May afternoon in Hartford, CT.

Meander Over to the Mark Twain House


Mark TwainMark Twain commissioned this Neo-Gothic mansion in 1873, at the height of his fame and fortune.


It was here that Mark Twain and his family lived some of their happiest years. It’s also where the writer penned some of his most famous works, including:

  • The Adventures of Tom Sawyer
  • The Adventures of Huckleberry Finn
  • A Connecticut Yankee in King Arthur’s Court


Unfortunately, due to a poor investment, Twain lost much of his fortune, and the family was forced to move to Europe.


Even after recovering his fortune, the family could not return to the house. After the death of one of their daughters, Mark Twain’s wife couldn’t bear to live in the house with those painful memories.


And so the house was sold.


But the museum curators refurbished the mansion to recreate the opulent days when Twain’s family lived here.


This museum is a major draw for fans of Mark Twain and architecture.


Make a reservation for a guided tour of the Mark Twain House, which is the only way to access the museum. The tour covers the three stories of the mansion, so be prepared to climb lots of stairs.

Enjoy a Day at Lake Compounce Amusement Park


The oldest amusement park that’s been in continuous operation, Lake Compounce is the home of a charming nostalgia for the summers of your grandparents’ childhood.


While classic attractions abound here:

  • A carousel
  • A ferris wheel
  • Wooden roller coasters


But the park continues to improve, with a recent addition being the largest water park in Connecticut.


And speaking of wooden roller coasters, enthusiasts voted Boulder Dash the best wooden roller coaster in the world.


Top Events across CT in May to Enjoy

May is the month in which the festivals and fairs in Connecticut go into full swing.


From food truck festivals to creative exhibitions and everything in between, below are our top picks for May events:


Art to the Avenue | Greenwich

Every May, visitors descend upon Greenwich, Connecticut, to see the artwork of more than 120 artists at the annual Art-to-the-Avenue festival. During this special event, Greenwich Avenue is transformed into a strolling gallery, complete with musicians, street performers, and lovely works of art for sale. You have to attend this Connecticut spring festival!


May Market | Farmington

Another festival that is highly anticipated is the May Market in Farmington. There are over 30 vendors selling a wide range of springtime plants and flowers.


Children under the age of 12 are admitted free to this farmer’s market, which charges a $10 admission fee per person.


At the beginning of May, the Hill-Stead Museum, one of the best things to do in Farmington, CT, hosts a festival that runs from late morning to mid-afternoon.


The annual Dogwood Festival | Fairfield

The Dogwood Festival in Fairfield, Connecticut, is one of the state’s largest celebrations. It features over 60 vendors in addition to live music, games, raffles, and a tag sale. If you get hungry while on your day’s adventures, there is plenty of food to try.


What began as a minor event has grown into a major one. Back in 1936, a small group of women organized the festival by setting up refreshments on a small craft table and selling handmade items. This festival will be held at the Greenfield Hill Church on a weekend in early May, usually around Mother’s Day in CT.


International Festival of Arts & Ideas | New Haven


The goal of this festival was to combine outstanding art with significant concepts. This popular summer attraction is modeled after European arts festivals. The Festival of Arts & Ideas aims to bring people together in an effort to strengthen social cohesion while celebrating diversity. In the charming city of New Haven, CT, enjoy the music and artwork of international artists.


Outdoor Crafts Festival at the Bruce Museum | Greenwich

Enjoy fine crafts and music at this museum-quality event at the Bruce Museum of Greenwich. This isn’t your mother’s arts and crafts show. Instead, it focuses on contemporary, high-end fine crafts created by regional artists. In addition to the museum’s exhibits, roving performers will entertain you.


Greenwich Town Party

The Greenwich Town Party has recognized the neighborhood’s and town’s history. Every summer, it serves as a way to rekindle the town’s affection. People travel from all over the world to Greenwich to take part in the festivities. Furthermore, the organizers have made every effort to make this one of Connecticut’s most exciting music festivals.


Discover More Hidden, Secret, Things to do in Connecticut in May


Connecticut is an ideal spot to escape, regardless of the time of year. Each season makes the state feel like an entirely new locale, which makes for entertaining road trips in CT.


So, whether you’re planning your visit to:


We hope you enjoy your time, exploring all the most unique things to do in Connecticut!

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