Refreshing countryside and coastal retreats — Connecticut is full of maritime history, picturesque inlets, lush forests, quaint towns, seafood, museums, and dozens of countryside vineyards.
Riverside Beauty - Essex
The colonial shipbuilding village 6-miles up the Connecticut River from the Long Island Sound and Old Saybrook is one of the few American towns attacked by a foreign power and the site of the second greatest naval loss in U.S. history with 28 ships burned or sunk — 10 more than Pearl Harbor.
Essex is charming with art galleries, quaint boutique shops, and the home of The Griswold, one of the oldest continually run taverns in the United States. The stunning 1817 Florence Griswold Museum in Late Georgian-style architecture with a modern art gallery and scenic gardens is a great spot to take a stroll on Lieutenant River. Plus the Connecticut River Museum and Essex Steam Train & Riverboat are enjoyable stops.
Countryside Explorer - Simsbury & West Granby
Driving through Simsbury and West Granby, the 19th century agricultural and tobacco farming past comes alive with active farmsteads, vineyards, and vegetable markets. Beautiful farmhouses, tobacco sheds, and New England style, English styles, and cross-gabled gambrel-roofed dairy barns blanket the countryside.
The area has the most unique farmstands including Flamig Farm home of the giant EGG spelled backward sign and petting zoo. The Holcomb Farm with 10-miles of nature trails and a farm store offering fresh and locally sourced artisanal bakeries, dairies, and organic vegetables or the fascinating Garlic Farm with layers upon layers of cured White German garlic displayed in historic tobacco shed. And the picturesque Rosedale Farm & Vineyard with great wine, beautiful scenery, and live music.
Enders State Forest with miles of hilly hiking trails, five distinct waterfalls, and popular swimming pools — and Talcott Mountain with beautiful ridge-line hiking, stunning panoramic views of the Farmington River Valley, and the 1914 Heublein Bavaria Tower standing 165-feet tall and 1000-feet above the valley are two great hiking areas.
Absolutely Delightful - Chester
North of Essex in the Connecticut River Valley, Chester is full of creativity, and the Chester-Hadlyme Ferry, is the second-oldest continuously operating ferry service in Connecticut. The historic downtown is unique with delightful art galleries, breweries, rustic taverns, markets, and specialty shops in historic mills and colonial homes. The hillside town is also surrounded by marinas, hidden streams, cascading waterfalls, thousands of acres of state forest, and hiking trails — including an Alpacas farm and Pattaconk and Eagles Landing State Park. Gillette Castle and Selden Neck State Park are a short ferry ride away.
Island Hopping - Stony Creek
The small historic district of Stony Creek is a gateway to the Thimble Islands, an archipelago consisting of dozens of small islands with summer cottages in the Long Island Sound. The largest is Horse Island owned by Yale University and maintained as an ecological laboratory by the Peabody Museum of Natural History. Kidd and Money Island are named after the famed pirate Captain William Kidd who looted ships throughout the Caribbean and Long Island — Kidd was rumored to hide his treasure on Money Island. There are a dozen more including Outer Island, the outermost and part of the Stewart B. McKinney National Wildlife Refuge.
The seaside town seems sleepy with a dock, a restaurant, and a small beach but the island community is active with sailing, boating, and kayaking — so get out on the water and explore.
Harborside Village - Southport
Once the center of trade and commerce, the historic village of Southport has one of the highest concentrations of Greek Revival and Victorian houses in the country. With over 150 historic buildings the most significant are Oliver Hazard Perry, a Greek Revival house with a pediment above four Doric columns — Walter Perry III, an 1830 Federal-style house — 1766 Meeker House, the only home to survive the British burning of Southport in 1779 — the Sheffield House is unique for being the home of a privateer for Argentina during its war for independence from Spain. The town is perfect for architecture lovers and harborside walks, cycling, and views of Long Island Sound — it is the prettiest town in Connecticut.
Countryside Living - Litchfield
Nestled between Bethlehem and Torrington, Litchfield was once home to American Revolutionary War Hero Ethan Allen and Elizabeth Gilbert author of Eat, Pray, Love. The Litchfield Historical District, located in the village green features Georgian, Victorian, and Greek Revival architecture style and is surrounded by vibrate shops and eateries. Tapping Reeve House Law School and Litchfield Historical Society are noteworthy museums to explore.
The town is surrounded by beautiful countryside including the White Memorial Conservation Center, Knife Shops Falls, Haight-Brown Vineyards, and Topsmead State Park. Topsmead the summer estate with Tudor Revival cottage is popular for nature walks, butterfly fields, and picnickers.
Maritime History - Mystic
Famous for the movie "Mystic Pizza" starring Julia Roberts — Mystic is the largest attraction in Connecticut with the premier maritime museum in the country with collections of historic watercraft and 19th-century seafaring villages. The village maritime trades are displayed in dozens of historic buildings and working shipyards. The shipyard gallery takes visitors through 40-years of restoration and preservation projects — including Mayflower II and Charles W. Morgan. The 1841 Charles W.Morgan whaling ship is the flagship exhibit—significant for being American’s oldest commercial ship still afloat, surviving blistering Antarctic ice and rounding the deadly Cape Horn.
The historic downtown and experience coastal culinary experiences, art galleries, and specialty shops. The1920 Bascule Bridge spans the Mystic River with iconic and instragramical industrial iron wheels. The water activities include paddleboarding, kayaking, sunset sailing—and more.
Seaside Charm - Stonington
Stonington’s seaside charm is a quiet getaway from Mystic and best experienced with a stroll on Water Street with weathered fishing docks, historic homes, boutique stores, art galleries, and restaurants.
The town's rich history in shipbuilding and West Indies trading was once the home of many sea captains and shipbuilders. Architecture lovers should enjoy exploring the dozens of Colonial, Greek Revival, Victorian, and Federal-style architecture houses — Oliver Smith House (1761), Charles Phelps William (1804), Gurdon Trumbull House (1837), and Williams-Pendleton House (1848) are noteworthy. Lovers of literature and poetry should visit James Merrill House at 107 Water Street — home of the American writer and Pulitzer Prize winner for Divine Comedies.
After strolling through the quaint streets enjoy the scenic coastal countryside at Jonathan Edwards Winery, Stonington Vineyards, or Saltwater Farm Vineyard — and sunset at Old Lighthouse at Stonington Point.
Military History - Groton
On the eastern shore of the Thames River, Groton's rich military history comes alive with U.S.S. Nautilus at the Submarine Force Museum, Avery Point Lighthouse, and Fort Griswold Battlefield. Fort Griswold, a former defensive fortification played important role in the American Revolution supplying the Continental Army and privateers who attacked British ships — Benedict Arnold who betrayed the American cause later raided, burned neighboring New London, and took the fort. As Colonel Willaim Ledyard surrendered, the commanding British officer took Ledyard's sword and killed him with it. British forces then slaughtered 80 surrendering American soldiers.
Beyond the historical and military importance of the town, the coastal reserve of Bluff Point State Park with the barrier beach, rocky bluffs, wetlands, and forested hillside has views to Fisher Island and New London Ledge Lighthouse. It is a beautiful park with one of the best beaches in Connecticut.
First Settlement - Windsor
Originally named Dorchester, Winsor is the first English settlement in Connecticut founded in 1633 and full of historic architecture with over 150 homes and buildings pre-dating the 1850’s.
including the Strong-Howard House, Chaffee House, and Windsor Locks Canal. The 1758 Strong-Howard House is notable, being a humble farmhouse in comparison to the other elegant homes in Windsor and Palisado Green. Capt. Howard was a revolutionary war sailor, savory character, and whose political views were often at odds with his neighbor's more refined lifestyle, including his wife Ann's wealthy upbringing and polite nature. The home fancy decor and odd configuration capture the complexities of these relationships against the humble architecture. The home is now a museum and Windsor Historical Society.
The Chaffee House (1767), Deacon John Moore House (1664), and Oliver Ellsworth Homestead (1781) are other notable historical landmarks for architecture lovers — and the New England Air Museum with over 100 early flying machines, modern aircraft, and supersonic jets tells stories of aviation is great for kids.
Pretty Houses - Farmington
Farmington lined with colonial homes and estates dates to the 17th century—George Washington referred to it as “the village of pretty houses” — and none prettier than Hill-Stead.
With a combination of art, architecture, and stunning countryside—the historic farm by Theodate Pope Riddle one of the first women architects in Connecticut includes 152-acres of gardens, nature trails, a museum, and beautifully landscaped meadows. Hill-Stead was her first architectural project and one of the earliest American country houses—considered the finest example of Colonial Revival homes in the United States. And featured in Architectural Review (1902), Architectural Record (1906), and American Home & Gardens (1910).
The Hill-Stead museum collection includes a series of impressive impressionist paintings from Edgar Degas, Claude Monet, Mary Cassatt, and Edouard Manet—original furnishing, textiles, decorative arts, photography, and ranges of Japanese, American and European prints, including an engraving by Albrecht Durer and etching by Henry Matisse.
The Sunken Garden is a popular outdoor gathering spot with seasonal beauty and more than ninety varieties of perennials. Inscribed in the stone walkway is the Latin phrase “Ars Longa, Vita Brevis”, meaning “Art is Long, Life is Brief”. Families can enjoy a leisurely stroll to Clatterridge Sheep Farm—or a more strenuous hike to Blue-Blazed Metacomet Trail. Beyond Hill-Stead Museum explore the 1720 salt-box, Stanley-Whitman House with museum, gardens, and apple orchids—or enjoy cliff-top scenic vistas and Warren's Den, a boulder cave located on Rattle Snake Mountain.
Riverside Adventure - Collinsville
Classic New England town on the Farmington River centered around the iconic Old Axe Factory — Collinsville is Connecticut’s coolest town with beautiful river walks, great eateries, and stunning countryside. The area is incredible for kayaking, paddle boarding—and the Farmington River Trail is great for cycling and long nature walks.
Strolling through town is the Canton Historic Museum, antique shops, famous La Salle Market, and delicious Francesca’s Wine Bar. Flamig Farm is on the outskirts of town and a great place to learn more about farm animals. Nepaug State Forest, Ender Falls, and Talcott Mountian Park are short drives — Tacott the former Heulblein summer estate with a Bavaria style tower standing 165-feet tall and 1000-feet above the valley. The tower is seen for miles in all directions. Ridgeline hike provides a stunning panoramic view of the Farmington River Valley.
Jewel of Inland Parks - Kent
Perfect for a weekend escape, Kent is famous for the Jewel of the Inland Parks — Kent Falls is a beautiful 250-foot cascading waterfall and great for families offering hiking, picnicking, and fishing — there are two short nature trails along each side of the falls with many lookout points.
The village is a few miles south is delightful with small specialty shops and delicious eateries — including the Sloane-Stanley Museum, Connecticut Antique Machinery Exhibit, and Bulls Bridge one of the last remaining covered bridges in Connecticut. Kent is full of outdoor adventures with miles of hiking at Macedonia Brook State Park, Pond Mountain Natural Area, and Iron Mountain Reservation — and nearby Lake Waramaug with stunning sunsets and great wineries is worth exploring.
Coastal Heritage - Waterford
A beautiful blend of outdoor living and rich heritage, Waterford was once the west farmland of New London and famous for Harkness Memorial State Park. The former estate and the summer home of philanthropists Edward and Mary Harkness who inherited a substantial fortune from Edward’s father Stephen V. Harkness, a silent partner in Standard Oil. During their lifetimes, Edward and Mary donated over $160 million ($2 billion in today’s dollars) to cultural, educational, and healthcare organizations. The historic preservation is 300 acres and centered around Eolia, a 42-room Renaissance Revival mansion with formal gardens, greenhouses, and views of the Long Island Sound with stunning sunsets.
Waterford is also home to the Eugene O'Neal Theater, Stenger Farm, Seaside Sanatorium, Waterford Beach Park, and Speedbowl — and only a few minutes from New London with charter boat fishing and lighthouse cruises.
The Famous Bridge - Cornwall
The "Greenest town in Connecticut", Cornwall is set in the Berkshire Mountains and is surrounded by steep hills, deep valleys, and hundreds of acres of dense forest land in the Mohawk State Park. The naturally secluded community encompasses the three townships of Cornwall Bridge, Cornwall Village, and West Cornwall — and is famous for the historic red-covered bridge and authentic country living. Cornwall is a beautiful place to get away from it all, enjoy the outdoors, and a short drive to Great Falls, Dean's Ravine Falls, and Mohawk Mountain Ski Area.
Shoreline Village - Guilford
The shoreline village settled in 1639 with a vibrant community and expansive 16-acre historic town green surrounded by gift shops, cozy homes, picturesque churches, and art galleries. The town has the oldest home in Connecticut and the oldest stone house in New England. Known as the "Old Stone House" by locals, Henry Whitfield State Museum is the most significant architectural house in Connecticut — and unique for its time in Colonial America due to the thick stone walls which served as a fort for protection.
The town marina with views of the Grass Island has a few eateries, including Guilford Lobster Pound voted the best Connecticut lobster roll for 2021. In the north, Bishop's Orchard is a favorite with the farmers market, ice cream, winery, and festive holiday events — and Strawberry Hollow Farm is a delightful little farm perfect for pumpkin patches and holiday gifts. The Place is a local favorite, a unique summer outdoor seafood restaurant with tree stump stools, a crackling wood fire that roasts savory clams, lobsters, sweet corn, and much more.
Arts & Beach - Milford
Vibrate artist and beach community famous for its summer PorchFest and Oyster Festivals, Milford has multiple beaches to enjoy from Silver Sands State Park to Walnut, Bayview, Gulf, and Wildmere Beaches — and many shoreline, harbor, beach, river, and wooded trails
Milford has the second-longest town green in New England; lined with monuments and war memorials dedicated to servicemen and women. The Lower Lagoon on the Wepawaug River is a scenic spot to fish and picnic. The town has a variety of delicious eateries such as The Greek Spot Cafe, Scratch Baking, and The Corner (People's Magazine's Best of Connecticut) — it is also home to the Connecticut Audubon Society Coastal Center. Milford is a wonderful blend of creativity, history, and nature.
For more on Connecticut visit Wine Country or Summer Seaports. Return for future posts on Great Coastal Escapes, Magnificent Florence, and much more.
Sources: Wikipedia
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