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For the ultimate scenic Connecticut Road Trip along the Shoreline, follow the Getaway Mavens turn by turn guide, which brings road trippers to the charming towns of the Southern New England coast.
Fans of country roads seeking one of the best drives in the Eastern United States will discover long tidal rivers, seeds of Yale University, and remnants of the Revolutionary War in our Constitution State.
When Ayn Rand needed to research The Fountainhead, when Katherine Hepburn yearned to escape the frenzy of Hollywood, when President Taft sought a summer home, they all came to this sliver of a small town on the Connecticut shore that many travelers miss.
Most assume that the industrial harbors seen while barreling north on Interstate 95 from New York to Boston define the Connecticut coast. But that isn’t so.
You’ll find salt marshes that spread like the Kansas prairie, sea-stained buoys that hang from weather beaten balconies, pink granite outcroppings, and breathtaking views of pristine coves and towns, all in the particular light that inspired the American Impressionist movement.
Begin Your Connecticut Road Trip in the Thimble Islands
If starting your Connecticut Road Trip from New York City, drive 90 miles north on I95 and get off at Stony Creek (Exit 56), just north of New Haven to begin your coastal drive. Spend a couple of days exploring the region that’s a bit Florida Everglades, a bit Maine Coast, but is singularly Connecticut.
From exit 56, drive 3 miles to the Stony Creek Town Dock to take a tour of the Thimble Islands on the Sea Mist with Captain Mike around the mauve-colored Thimble Islands, named for the prolific Thimble Berry, not their size.
Together, the Thimbles consist of over a hundred islands of various sizes, some are no bigger than a stepping stone, others large enough for 32 houses.
About a mile away, Stony Creek Quarry still turns out the same stone upon which Thimble Island homes, both baronial and whimsical, sit. Chunks of “Stony Creek Pink” form the base of the Statue of Liberty, the abutments of the George Washington Bridge, and the entire AT&T Building in New York.
While researching for her book, The Fountainhead, Ayn Rand lived in Stony Creek, gleaning background information for the main character, Howard Roark, who takes a job in a Connecticut quarry. Grab a bite at either Stony Creek Market or Thimbleberry Café, and peruse the gifts, jewelry and housewares at Seaside Shop.
Plan a weekend getaway with our Thimble Islands travel guide.
The Perfect Segway In Guilford CT
Guilford is best known for the Henry Whitfield House, the oldest home in Connecticut with the oldest stone home in New England. The Guilford Town Green was once grazing area, graveyard and fairgrounds- where tourists now swarm booths at annual craft and lobster festivals.
To get the best overview of Guilford’s historic homes and shoreline, join an educational and fun Shoreline Segway Tour.
This “a walking tour in fast-forward” takes you past colonial houses, through the Guilford Town Green then out to the harbor to see sweeping views of salt marsh, Osprey nests, and shore birds diving into the water like crashing kites.
Afterwards, if it’s a nice day, drive east on Route 1 about ½ mile to The Place, an outdoor, seasonal barbecue spot which counts Will Ferrill and Martha Stewart among its fans. Beefy guys, presiding over a humongous flaming grill, char ribeye, salmon, clams, and corn to perfection.
Plan a weekend getaway with our Guilford CT travel guide.
Kayaking and The Best Lobster Roll In New England
Bone up on American history trivia at the 1630 House, (now the Tourist Information Center).
You’ll learn, among other things that Yale College was established in Clinton in 1701 (before money was endowed to build a permanent campus in New Haven), and emerging Postmaster General Benjamin Franklin placed a milestone on the “Post Road” – now Main Street – in the 1750’s.
To get a feel for the coastline and serpentine inlets, rent a kayak, life vest and laminated map at Indian River Marina. from which you can paddle the winding, weeping-willow studded Indian River into Clinton Harbor and up the grassy Hammonasset River, gliding past Ospreys, Herons, Cormorants and a plethora of gulls.
Need a snack? Down the street, gobble up an award-winning lobster roll—a simple toasted hoagie roll brimming with chunks of lobster drizzled with butter—at what is arguably one of the last authentic lobster shacks in Connecticut, Lobster Landing.
A few miles up the road in Madison, you’ll find the RJ Julia Booksellers, a fantastic indie bookstore that for over 25 years has put this town on the map. If you are so inclined, bed down at the Madison Beach Hotel – the only sandy beachfront luxury lodging on the Connecticut Coast.
Plan a weekend getaway with our Clinton and Madison CT travel guide.
Stop By Katherine Hepburn’s Haunt
From Madison, drive 5 miles northeast on Route 1 past faded motels, strip shopping centers and the myriad marinas of Westbrook where thickets of masts create the illusion of forested coves.
Turn right on Route 154 towards Old Saybrook Shore Points crossing causeway bridges, and traversing neighborhoods where relatively modest homes front an ever widening Long Island Sound.
One of these neighborhoods is Fenwick, where actress Katharine Hepburn lived in her beachfront mansion until her death at the age of 95.
Take in a show at the Katharine Hepburn Cultural Arts Center in the center of town. The Kate, as the Arts Center is affectionately known, hosts dance, theater, opera and film events in a cozy 250-seat auditorium.
Stay at the antique-filled Saybrook Point Inn and Spa (which provides discounted tickets to The Kate) for great marina and Sound views, or in one of Saybrook Point’s two new “Boutique Inns” – Three Stories or Tall Tales across from the main property. Plan to have dinner at the wonderful in-house Fresh Salt Restaurant or in town at Liv’s Oyster Bar.
Plan a weekend getaway with our Old Saybrook CT travel guide.
End Your Connecticut Road Trip in the Lyme Light
Alternately, you can jump onto I-95 North and cross the Connecticut River to Old Lyme for some French refinement at the swanky nine-room Bee and Thistle Inn, and onsite Chestnut Grille restaurant, a favorite of celebrity chef, Jacques Pepin.
Old Lyme remains a thriving art colony and bird watching paradise (modern-day Audubon, Roger Tory Peterson – of the Peterson’s Field Guide to Birds fame – lived here). Each morning, fog creates the hazy tableau of an impressionist painting; a blurred, muted landscape in the very place considered the birthplace of American Impressionism.
You can easily spend a day at the Florence Griswold Museum, a compound that includes the Georgian-Style main house, a modernist gallery building, a barn studio, and acres of gardens and plantings set on the Zen-serene Lieutenant River.
In the mid 1800’s, to keep from loosing her home after her husband died, Florence Griswold rented rooms to artists drawn to the brilliance and clarity of light in Old Lyme. Childe Hassam, Henry Ward Ranger, and dozens more moved in and painted on everything within sight, including Griswold’s cupboards and doors.
You can still see these preserved cabinets during the main house tour along with hundreds of paintings on exhibit there and in the museum’s separate Krieble Gallery.
But don’t leave before taking canvas, smock and palette (all provided in the price of admission on Sunday afternoons) behind the studio to the meadow-like banks of Lieutenant River to fulfill your Monet fantasies in the exact spot where American Impressionists were inspired. You’ll jump back onto frenetic I-95, with a greater understanding of the artistic appeal and beauty of the Connecticut Coast.
Extend your Connecticut Road Trip with our Old Lyme CT travel guide.
Weekend Getaways on the Connecticut Coast
- Thimble Islands: Favorite of Presidents, Tom Thumb, and Ayn Rand
- Guilford CT: Seeds of “Offbeat” Northeast
- Recharge Your Soul In Clinton and Madison CT – with the Best Lobster Roll In New England
- Old Saybrook CT: Kate Hepburn’s Hangout on the Connecticut Shore
- Old Lyme CT: Birthplace of American Impressionism
A version of this article was published in National Geographic Traveler April 2011.