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14 Top-Rated Things to Do in Connecticut

Written by Shandley McMurray
Oct 9, 2020

Despite its small size (it's the 3rd smallest of America's states), Connecticut overflows with New England charm. White picket fences, verdant landscapes, sprawling lakes, sandy beaches, and thundering waterfalls blanket the state, wowing visitors with their innate beauty. Bigger cities offer tourists the larger museums, theaters, and fine dining they crave, while smaller towns feature quaint shops and waterfront cafés.

Tying all these together is a natural backdrop so beautiful, you'll never want to leave. Whether it comes in the form of a sprawling park nestled among high-rises, soft waves caressing a shoreline, or trails winding their way through dense forests, the area's splendor is captivating.

While spending time in these natural environments is a favored pastime, Connecticut offers a slew of other attractions to keep visitors entertained -from stepping back in time at the Mystic Seaport to riding a steam train in Essex to soaking up knowledge at the museums of New Haven.

To help you decide where to start your journey in this dazzling New England state, read this list of the best things to do in Connecticut.

1. Spend a Day in Mystic

Mystic, Connecticut

If you're looking for a picturesque spot to soak up some history, sail along a quiet harbor, and fill your belly with tasty treats, you'll find it in Mystic. An adorable coastal town set along the Mystic River, this charming retreat is a perfect place for a weekend getaway.

Spotted with gleaming sailboats, the town thrives on its nautical history. Once serving as a port for whaling vessels, the popular Mystic Seaport is one of the best museums in Connecticut. Boasting everything from a planetarium to a working shipyard to historic wooden ships and a 19th-century seafaring village, you'll need at least a day to fully explore its offerings. Don't worry, there's a restaurant on-site to help quiet those grumbly tummies.

The Mystic Aquarium is also top-notch. In fact, it's been deemed one of the best attractions in Connecticut. People come for the beluga whales but stay for the other impressive creatures and exhibits.

Don't miss a visit to the Olde Mistick Village, and make sure you're hungry when you arrive. An outdoor mall designed to represent a 19th-century New England Village, the charming area is filled with themed stores, most of which offer free samples of their delicious wares. With multiple eateries on site, this is one of the best places in Connecticut to visit for a meal.

Accommodation: Where to Stay in Mystic

2. Take the Ferry to Gillette Castle

Gillette Castle

The Chester-Hadlyme Ferry takes visitors (and their cars) from the adorable small town of Chester, across the Connecticut River to Hadlyme, home of the unique Gillette Castle.

While this is a popular route during the warm, summer months, the most beautiful time to book this short, five-minute ride is during fall. Spectacular red, orange, and yellow hues are reflected in the sparkling lake as the trees climb the hilly shores known as the Seven Sisters.

Once back on land, be sure to visit the castle (technically in East Haddam). Built in the early 20th century by stage actor William Gillette, the 184-acre estate offers spectacular views of the river below. The medieval Gothic castle itself contains secret passageways, intricate locking mechanisms, and other whimsical treasures designed by the creative Gillette.

3. Ride the Coasters at Lake Compounce

Phobia Phear Coaster at Lake Compounce | JJBers / photo modified

For some, there's nothing like a thrill ride to complement a vacation. Heart-pounding adventures aboard flipping roller coasters encourage squeals of delight along with screams of sheer terror. Boulder Dash, an award-winning wooden coaster is unmissable, while the Phobia Phear Coaster, which gets up to 65 miles an hour, will cause you to tighten your grip.

If coasters make you feel more like tossing your lunch than euphoric, there are plenty of other more low-key options to keep you entertained. The classic carousel is an all-time fave, as is the giant Ferris wheel, and Flying Elephant ride.

When the day's too hot to handle, head to the on-site water park. Bayou Bay offers a well appreciated break from the hot summer sun, while the Croc-O-Nile lazy river is the perfect way to relax. Hop in a tube for a fun way to plunge down a waterfall at Mammoth Falls.

4. De-Stress in Chester

Shops in Chester | Doug Kerr / photo modified

Although small, Chester has an incredible calming effect on even the most stressed of travelers. Wandering though its lovely streets is akin to getting a nice, warm hug.

Located nearly two hours from both New York and Boston, this quaint hamlet is a popular weekend destination for city dwellers looking to unwind. It's set upon the Connecticut River and is home to kind and welcoming locals who serve up a mean brunch (and dinner) at the town's eateries.

Lovely 19th-century-era buildings line Chester's streets, harkening back to the days when this little village survived through trades like shipbuilding and milling. These downtown buildings have been well kept, preserving the town's history and adding to its allure.

An artsy place, Chester is filled with artisan's studios, gift shops, and galleries. Maple & Main Gallery of Fine Art is one of the area's most popular, with a prime spot in the center of town.

Accommodation: Where to Stay in Chester

5. Climb Aboard the Essex Steam Train

Essex Steam Train

Chugga, chugga, chugga! Find a seat and get comfy on the Essex Steam Train. An antique train featuring vintage coaches, this fun ride allows visitors to roll their way along the splendid Connecticut River Valley.

Guided by an enthusiastic conductor, you'll learn historical facts while traveling from Essex Station (circa 1892) on the 12-mile round-trip journey. Along the way, you'll pass the sweet towns of Chester and Deep River, which up the charm factor.

Add a Riverboat tour to your ticket to prolong the scenic adventure. The Becky Thatcher riverboat will take you on an unforgettable cruise highlighted by glimpses of impressive wildlife (i.e. bald eagles and herons), beautiful shoreline, and historic sites like the Gillette Castle and Haddam Swing Bridge.

6. Hike the Trails in Kent

Kent Falls

A day spent in Kent Falls State Park is the ultimate cure for stress and anxiety. You'll feel your shoulders relax upon your first inhalation of the area's fresh, clean air.

The park, which is set in the Litchfield Hills, is a magical wonderland filled with the most spectacular beauty. Waterfall? Check. Covered bridge? Check. Verdant forest? Check. Told you it's packed with gorgeousness, and trust us; you'll want to pack a picnic because you won't want to leave.

The breathtaking Kent Falls cascades down 250 feet. Hike to the top (don't worry, it's not too tenuous a walk) for the best views and the reward of a cooling mist upon your face. Watching the water tumble to its temporary resting place, Falls Brook (a tributary leading to the Housatonic River), is incredibly relaxing.

7. Go Fishing in Madison

Calm fishing waters at Hammonasset Beach State Park, Madison

It's easy to miss this adorable spot, a tiny coastal town located about halfway between New York and Boston. Its perfect location, butting into the Long Island Sound, makes this a great jumping-off point for expectant anglers.

Head out to sea on a fishing charter or drop your line at Meig's Point Jetty or West Beach Jetty at Hammonasset Beach State Park. Spanning two miles of coast, this lush spot is the longest shoreline park in the state. Nearby Madison Lake ups the ante that you'll reel in a big one.

When you're sick of casting a line, head into town to soak up the historic charm and grab a bite to eat at one of the family-owned restaurants. Main Street is endearing, lined by preserved historic buildings dating back to the mid-1930s, and often the site of a farmer's market and outdoor concerts when the weather turns warm.

Accommodation: Where to Stay in Madison

8. Get Inspired at the Yale University Art Gallery

Tribal masks at the Yale University Art Gallery | VillageHero / photo modified

New Haven is home to Yale University, a bevy of impressive museums, and an increasingly popular restaurant scene. While the Yale Peabody Museum of Natural History is a must-see for those jonesing for a dinosaur or sarcophagus sighting, the city boasts another gallery that will take your breath away.

Tucked off the main green, the Yale University Art Gallery features more than 250,000 objects, including masterpieces crafted by, well, masters. You'll find works by the likes of Degas, Monet, and Manet within these spacious walls. The gallery features timeless art and artifacts on display from across the globe. Regions such as Asia, Europe, and the Indo-Pacific are all represented here.

Not a fan of the classics? Not to worry. The gallery boasts an impressive collection of modern and contemporary works to keep you entertained. The best part? Entrance is free!

9. Photograph the Covered Bridge in West Cornwall

The West Cornwall Covered Bridge in winter

Covered bridges emanated romance long before Clint Eastwood wooed Meryl Streep in The Bridges of Madison County. The pitched rooves and brightly painted wooden walls create a captivating backdrop. Add a flowing river below and established trees along the banks, and your camera will beg to start snapping. This is one of the most beautiful places to photograph in Connecticut.

If you're a fan of these charming structures, don't miss the West Cornwall Covered Bridge. One of the final remaining covered bridges in the state, this 172-foot masterpiece harkens bridge lovers from across the globe. Its warm red siding brightens the surrounding landscape as it spans the rushing Housatonic River.

Insider's tip: Hire a bike from Covered Bridge Electric Bike Rental. Located a mere 100 feet from the bridge, the friendly staff will help you get oriented with your electric powered, zero emissions bike and guide you to the area's best cycling trails.

10. Sunbathe at Hammonasset Beach State Park

Hammonasset Beach State Park

Home to more than two miles of soft, sandy beach, there's plenty of room to spread your towel at Hammonasset Beach State Park. Located along the shores of the Long Island Sound in Madison, this park boasts the largest shoreline in the state. It also tops the list of best beaches in Connecticut.

While the park's most popular pastimes include, sunbathing, boating, fishing, sandcastle-building, and swimming, there are a ton of other activities to occupy your time at this incredible beach. Kayaking, scuba diving, SUPing, and visiting the Meigs Point Nature Center will keep everyone happy.

When it comes time for a break from the heat, head to one of the sheltered tables at the concession stand. Insider's tip: book one of the park's 500 campsites to extend your outdoor adventure.

Address: 1288 Boston Post Road, Madison, Connecticut

Official site: https://portal.ct.gov/DEEP/State-Parks/Parks/Hammonasset-Beach-State-Park

11. Cruise around the Thimble Islands

Thimble Islands

A sliver of paradise exists in the form of an archipelago in Branford. Beautiful homes ranging in size from tiny cottages to sprawling mansions dot the Long Island Sound, spread between 23 of the over 100 islands.

Actually, there's a great debate about how many isles make up the Thimble Islands. Some believe the number to be closer to 365 - it all depends on what you think is a "rock" versus an "island."

The largest, named Horse Island, covers 17 acres and is owned by Yale University, who uses it as an Ecolab for the Yale Peabody Museum of Natural History. The best way to discover this unique locale is by boat.

Insider's Tip: Book a Thimble Islands Cruise aboard the Sea Mist for a fun and informative tour.

12. Ogle Enders Falls in Granby

Enders Falls

Few activities are as relaxing as watching a waterfall. These impressive cascades often start out large and thunderous, as gallons of water thunder over rocks worn away by their constant presence. By the time the water reaches the pool below, the cascade has thinned and quieted, harmonizing as it joins the catch basin for a ride to its ultimate destination.

If you're truly lucky, you'll find a fall as captivating as Enders Falls in Granby. A natural marvel, this spectacular sight splits into five separate waterfalls. The first is six-feet tall, followed by three shorter, more gentle cascades that evoke a staircase. The final, most calming fall consists of two drops of 15 feet.

It ends in a cool swimming hole popular with summer visitors. No wonder it's deemed one of the best waterfalls in Connecticut.

13. Swim or Scuba Dive in Candlewood Lake

Candlewood Lake

What better way to spend a day than on (or in) the water? Boasting more than 3,000 lakes, ponds, and reservoirs, Connecticut is a great place to practice your cannonball. At 16 miles in length and 8.4 square miles in size, Candlewood Lake is one of the state's largest and arguably most beautiful lakes.

Created by the Connecticut Light & Power company in the late 1920s, this man-made reservoir is a hot spot for summer fun. Swimming, boating, fishing, kayaking, and all types of water sports top the list of things to do in this vast watery world.

Scuba diving is another popular activity. While the visibility is often low, there are a ton of interesting artifacts to be found on the lakebed.

14. Eat Local at Westport Farmers' Market

Strawberries for sale at a farmers market in Connecticut

An easy commute from Manhattan (it takes about an hour on the Metro-North from Grand Central), Westport offers locals and visitors a welcome slice of tranquility. Dipping into the Long Island Sound, the town's Compo Beach is a well-loved gem, as is the newly renovated Westport Library, which boasts a lovely path along a peninsula and unbeatable views of the Saugatuck River.

Every Thursday from mid- May to November, you'll find the bustling Westport Farmer's Market, which was conceived by Paul Newman (yes, that Paul Newman) and Michel Nisan in 2006. The market lies tucked away in a parking lot, across a small bridge on the other side of the river from the library. In addition to local fruits, veggies, and kombucha, you'll find freshly made tacos, a pizza truck, live music, art, and so much more.

Address: 50 Imperial Avenue, Westport, Connecticut

Accommodation: Where to Stay in Westport

Official site: https://www.westportfarmersmarket.com/

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