Connecticut – The Eastern Shoreline of Long Island Sound
The eastern shoreline of Connecticut, east of the main cities of Bridgeport and New Haven, offers the first real taste of rural New England for those arriving from New York. Near the grand mouth of the Connecticut River, there's a great number of historic towns lining the jagged coastline of Long Island Sound. Along Highway 95, you'll find a series of charming small historic towns, breathtaking nature sites, and even resort towns with popular sandy beaches bustling with visitors on hot summer days.
How much time do you need for a trip to the eastern shoreline of Long Island Sound?
It's recommended to dedicate at least a full day trip to the Connecticut shoreline east of New Haven. For a trip along the entire Connecticut coastline, including New Haven and the cities on the western shore of Long Island Sound, you'll need at least two full days of exploring.
It's highly recommended to find accommodations in New Haven, which is right in the middle of the Connecticut shoreline route
Click here to check availability and prices at New Haven hotels…
8 Must-See and Must-Do Things on the Eastern Shoreline of Long Island Sound
- New Haven and the Yale University campus
- A surreal experience at Gillette Castle
- Seals in their natural habitat in the Thimble Islands
- Seals not in their natural habitat at the Mystic Aquarium + the spectacular whale shows
- Learn about the period at the Henry Whitfield State Museum in Guilford
- The charming beaches of Madison Center
- American Impressionism in Old Lyme
- A stroll in the Essex Marina
Click here for the complete guide to traveling in the state of Connecticut…
What is the Eastern Shoreline of Connecticut?
- Unlike the state's western coastline, Connecticut's eastern shoreline is more rural in nature
- The large urban belt stretching from Manhattan to the suburban spaces between Greenwich and Bridgeport is interrupted by the city of New Haven and eastward from there
- The coast is characterized by small towns and cities, large river estuaries, and an indented coastline
- Between New Haven in the west and Rhode Island in the east, you can see Connecticut's most New England side
- In the realm of small towns with ancient mansions touching the strait's waters, natural sites featuring seals, massive river estuaries, and all the fun of nature, sea, and water
How to Plan a Road Trip Along the Eastern Coastline of Long Island's Bay?
Exploring the small towns and cities along the eastern coastline can be done via the two main travel routes in the area:
- The I-95 highway runs along the entire coast between New Haven and Providence in Rhode Island,
- In parallel to I-95, but much slower and safer, is the route of Highway 1
You can combine your outdoor trip with an urban one in the cities of New Haven and Hartford, the capital of Connecticut, and from there, continue towards Rhode Island and further to Cape Cod.
The most beautiful time to explore the area is towards the end of summer and the start of autumn, when the visitor crowds thin out a bit and you can start to see the sparkling fall leaves of New England in the forests alongside the grand rivers.
For planning a travel route in Connecticut and professional advice, click here…
Map of All Attractions on the Eastern Shore of Connecticut
Hotels and Lodging on the Eastern Coastline of Long Island Sound
- The main lodging area along the eastern coastline of Connecticut is the city of New Haven
- The city is located within an hour's drive from the Rhode Island border. You can also take a trip to the area from Providence, the capital of Rhode Island
- In downtown New Haven, in the streets south of New Haven Green, there is a range of good urban hotels rated three and four stars
- Some of the hotels in central New Haven are privately owned, but there are also several hotels belonging to major chains like Marriott
Click here to find accommodations in the hotels and motels of New Haven…
Another lodging option in New Haven, aside from urban hotels, is motels:
- Motels are the preferred lodging option throughout the USA (except for New York City and Manhattan) and are directly tied to the layout of the highways
- Motels near New Haven are located close to Interstate 95 and its split to 91, right near downtown New Haven
- The motels offer the best deal in America, with large rooms, often with 2 queen beds, breakfast, and of course, parking
- Many major hotel companies have motels near New Haven including Super 8, Best Western, and the Marriott and Hilton brands. There are also many motels along the route of Highway 95 and Route 1
- For those looking to combine with higher standard hotel stays, it's recommended to stay at the Foxwoods Resort and Casino, not far from Norwich (Click here to find accommodation near Foxwoods Resort and Casino…)
New Haven and Yale University
New Haven and Yale University are practically one unified urban entity. Yale is perhaps one of the world's leading and most famous universities, located right in the heart of New Haven, and its campus is really part of the city's fabric. Yale was founded by a group from Harvard University, and both have since been regarded as some of the world's most important universities.
New Haven itself is a charming university town, with a small downtown area where tall buildings cast shadows over the 18th-century structures that remain from the historic city. The city and the university campus boast numerous excellent museums, green parks, and fascinating buildings.
Click here for all the information about a trip to New Haven and the Yale University campus…
Everything to See and Do on the Eastern Coastline of Long Island Sound
Thimble Islands
About a fifteen-minute drive east of New Haven lies the gateway to the Thimble Islands. The Thimble Islands are a chain of islands near the Connecticut shoreline, in the Long Island Sound, which have become a tourist destination. You can sail to the islands from Stony Creek Beach, where a series of companies run boat tours among the islands.
On the small islets, you can see the New England nature in all its glory, including seals basking on the rocks, tiny green islets, and here and there local fishing cottages. The Thimble Islands boat tours are considered a popular attraction combining fresh air and nature.
Guilford
The small town or city of Guilford is located a twenty-minute drive on I-95 from New Haven. It is one of the oldest settlements in Connecticut, founded by British Puritans in 1650.
The small town is now home to twenty thousand people, many of whom arrived with the building boom in the 1970s when the little village practically became a suburban area of New Haven. At its center, Guilford retains the charming small-town atmosphere of New England that characterizes it so well. Its main street, Whitfield, is lined with lovely houses, numerous restaurants, and galleries. On the other side, there's a large green park.
The central site in Guilford is the Henry Whitfield State Museum. This period museum is housed in an impressive mansion from the late 17th century, filled with artifacts and furniture from the old town. Throughout Guilford, there are colonial period homes like the bright red Hyland House from the late 18th century, and further down the street, the charming Thomas Griswold House.
To the south, at the shore of Long Island Strait, lies the charming Jacobs Beach. This pastoral sandy beach is a favorite among the locals. It's like a preview of the trendy and popular beaches of neighboring Madison.
Madison
The resort town of Madison is among the most popular spots in New England for summer vacations. During the months of July and August, this town and its stunning beaches are packed with visitors who come to spend their entire summer here. Madison is a ten-minute drive east from Guilford on the I-95. Madison itself is situated north of the highway, but to the south towards the shore lies Madison Center, the lively and popular resort area near the beach.
The popular beaches in the town are Garvan Point Beach and the long Madison Beach. Right next to them, you'll find sports and recreation facilities as well as large golf courses. The town's center is on Route 1, known as Boston Post Road. Along it, there are galleries, seafood restaurants, and antique shops (and of course hotels). Just a bit east of the center is the stunningly beautiful Hammonasset Beach State Park, a natural beach stretching out into the Long Island Sound. During the summer, the park is a popular camping site and the beaches of the cape are known for snorkeling.
Essex
The town of Essex is one of the most perfect places in New England. It rests on the western bank of the mighty Connecticut River, just a fifteen-minute drive from Madison, and forty minutes from both New Haven and Hartford, the state's capital. The center of Essex, known as Essex Village, stretches on a sort of peninsula that juts into the broad riverway. The village's main street is Main Street, lined with charming houses and a handful of restaurants and shops.
North of the main street, at the end of Pratt Street, is the Essex Marina, teeming with fishing boats, houses, and cabins. There you’ll also find the Connecticut River Museum, which tells the history of the town. The museum highlights the era when shipyards in the town built vessels, with the fascinating display of the Turtle, the first submarine in history built in 1775.
Gillette Castle State Park
About a twenty-minute drive north of Essex, on the eastern bank of the Connecticut River, you'll find perhaps the most famous site in this part of New England. The almost surreal Gillette Castle is a must-see, stunning in its beauty. The castle was built in 1919 as the home of actor William Gillette.
The owner of the castle wanted a place inspired by the ancient castles of Europe. So, in the breathtaking and wooded area above the grand river, rests a castle that somewhat reminds one of Europe, yet feels much more like Disneyland. It is entirely made of granite stones and wood. The exterior features elements borrowed from medieval castle construction, but the interior is the realization of Gillette's ideas and fantasies. The castle's central hall, adorned with oak wood and dark fabrics, is slightly unsettling and quite intense. The courtyards and balconies of the castle offer a spectacular view.
Address: River Rd. 67, East Haddam
Click here for the castle's hours and park entrance fees…
Old Lyme
The town of Old Lyme is located just a 10-minute drive east of Essex, on the eastern bank of the Connecticut River. This pastoral town is best known as a central site in Connecticut for the American Impressionist School. This group of artists, in the late 19th century, moved through and painted the Connecticut coastline. During this period, the town became a popular summer artists' colony and a gateway for artists to paint the river's estuary landscapes. At the Florence Griswold Museum, located north of the town center, you'll find an impressive collection of paintings by artists from the school.
New London
Just a fifteen-minute drive from Old Lyme, along the banks of the Thames River, lies (how could it not?) the city of New London. New London is the bustling city of the rural area in eastern Connecticut, home to nearly 30,000 people. Downtown New London is sprinkled here and there with old houses from the mid-18th century, which survived the infamous burning of the city by the legendary American traitor Benedict Arnold. After being rebuilt, the city became one of the important centers in New England for whale hunting, much like the towns of Cape Cod.
Mystic
The town of Mystic is just a ten-minute drive east from downtown New London. The town is best known for its large aquarium, Mystic Aquarium, which has become a popular attraction. The aquarium's stadium can accommodate nearly 15,000 people and offers whale shows. The aquarium itself features thousands of species of fish and other sea creatures. There is also a pool for penguins and seals.
About a twenty-minute drive north of Mystic is the Foxwoods Resort and Casino, home to one of the largest casinos in New England. Apart from the giant casino, the resort offers entertainment options, restaurants, shopping, and an adjacent large golf course.
Mystic Aquarium address: Coogan Blvd. 55, Mystic, CT
Click here for all the information on the aquarium's opening hours and entrance fees…
