Travel
5 CT Road Trips: ‘Gilmore Girls,’ Glass House, Wooden Whaling Ship
With enough advance planning, a Connecticut road trip can include an overnight stay at a lighthouse. Also, check out Mark Twain's digs.
CONNECTICUT — At only 70 miles wide and 110 miles long — 5,545 square miles in all — Connecticut is made for road trips. The third-smallest state in land mass, Connecticut is the fourth-most densely populated of the 50 states.
The Constitution State has 170 small towns, and any one of them is easy to get to on a road trip. Here are five suggestions:
Road Trip Like The ‘Gilmore Girls’
Rural communities in northwest Connecticut provided some of the inspiration for “Gilmore Girls” Rory and Lorelai, who made their home in the fictional town of Stars Hollow, Connecticut.
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For your own “Gilmore Girls Getaway,” take a swing through Washington, New Milford, Bantam and Litchfield. The influences of all four communities are reflected in the show, but Washington is “Gilmore Girls”-central. The show’s creator, Amy Sherman-Palladino, fell in love with the town when she was staying at the Mayflower Inn & Spa and used it as a model for Stars Hallow.
While you’re in Washington, be sure to take a walk on the Henry David Thoreau Footbridge. Then, grab a coffee or late breakfast at Marty’s Café (or Luke’s Diner in the show). As you travel along CT-109W, you’ll pass some of the other sites familiar in the show, including The Washington Food Market (Doose’s Market) and The Hickory Stick Bookshop (Stars Hollow Books).
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From there, hop on CT-202S and head to New Milford, where you’ll see a green-topped gazebo that inspired the one in Stars Hollow. The Green Granary offers farm-to-table organic lunches.
From there, head to CT-67E back toward Washington, but take a couple of detours to the Bridgewater Village Store in downtown Bridgewater for some famous Bridgewater Chocolates, local honey and maple syrup, and if you want to play your “Gilmore Girls” role authentically, more coffee, before heading back to Washington for the night.
In the morning, head north on CT-47 and merge onto CT-202N to Bantam, where you’ll be able to shop at the Housatonic Trading Company and the Old Carriage Shop Antique Center and have ice cream at Arethusa Farm (Taylor’s Soda Shoppe in the show). Then make your way to the quaint town of Litchfield for more shopping.
Don’t Throw Stones
New Canaan, one of Connecticut’s wealthiest towns, was established as a Congregationalist parish in 1731 and wasn’t incorporated until 1801. The railroad’s arrival in the late 1800s transformed the shoemaking town into an enclave of summer homes for wealthy New Yorkers.
New Canaan became an important center for modern architectural design in the 1940s, when the “Harvard Five” brought mid-century modernism to town and built about 80 homes. One of them, Philip Johnson, designed the Glass House, where he lived from 1950 until his death in 2005. Now a National Trust for Historic Preservation property, the Philip Johnson Glass House is open to the public.
Many of the town’s Colonial buildings have been restored. About 20 of the mid-century homes were razed, but officials are trying to preserve the others, many of which were featured in the 1997 film, “The Ice Storm.”

Grace Farms, a humanitarian and cultural center on 80 acres, offers a wide range of free programs pursuing peace through nature, arts, justice, community and Design for Freedom, a movement that aims to end forced labor in the building materials supply chain and create a more equitable future.
New Canaan’s downtown is brimming with restaurants, boutiques and other stores — and don’t be surprised by a celebrity sighting or two. The Town Players of New Canaan, a community theater group formed in 1946, has a year-round production schedule.
The Carriage Barn Art Center changes its exhibits every month, featuring both juried and local artists, and also offers a slew of workshops from fine arts to bottle painting, as well s events and lectures.
New Canaan also has plenty of places to explore nature, including Waveny Park Conservancy and the New Canaan Nature Center.
New Canaan is located about 40 miles southwest of New Haven via I-95S and CT-15S.
Check Out Mark Twain’s Digs
Mark Twain may have set some of his most famous works, including “The Adventures of Huckleberry Finn” and “The Adventures of Tom Sawyer,” along the Mississippi River, but he wrote them from his home in Hartford, now the Mark Twain House & Museum.
The home, a National Historic Landmark, hosts activities and educational programs that illuminate Twain’s literary legacy and provide information about his life and times.
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Sam and Olivia Clemens (Mark Twain is the author’s pen name) moved into the home in 1874. They lived there until 1891, when they moved to Europe. The Clemenses sold the home in 1903.
The Harriet Beecher Stowe Center nearby at 77 Forest St. keeps the “Uncle Tom’s Cabin” author’s literary life alive. Inside are artifacts from her life, as well as interpretive exhibits of merchandise and playbills based on her novel, including how it was “re-interpreted” in the southern U.S. due to a lack of copyright laws or editorial control.
While you’re in Hartford, check out the Bushnell Park Carousel; the Bushnell Garden Sculpture Park; Stegosaurus, a 50-foot tall sculpture designed by Alexander Calder, one of the most important sculptors of the 20th Century; the Connecticut Science Center; the Soldiers and Sailors Memorial Arch; and other attractions.
Be sure to set aside some time to visit the Pratt Street Historic District, which holds street events year-round. Spend some time at one of the public bistro tables and check out the hilarious and interesting inscriptions engraved on sidewalk bricks beneath your feet. Among them is one that announces, “I can see up your skirt.”
Spend A Night In A Lighthouse
You’ll have to plan ahead for this one, but Greens Ledge Lighthouse in Norwalk offers a unique experience for up to six people that helps fund its preservation.
The offshore lighthouse was classified as “deteriorated” when preservationists began a five-year project to restore it. Even if you can’t book an overnight stay, public tours are available.
The Sheffield Island Lighthouse in Norwalk also offers tours both of the lighthouse and the keeper’s home, as well as a walk along the nature trail.
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From Norwalk, head up the coast to see the Stonington Harbor Light, a lighthouse turned historical museum at the tip of the Stonington Borough near Mystic. The lighthouse is accessible by ferry, and visitors can climb the old iron steps of the tower for an exceptional view.
Connecticut has 14 working lighthouses. Most not open for public tours but are visible by boat.
Experience America’s Seafaring Past
The Mystic Seaport Museum is not only the nation’s largest maritime museum, its 500 historic watercraft include four National Historic Landmark vessels, including the world’s last wooden whaling ship, the Charles W. Morgan. It’s also the oldest commercial ship still in existence.
The museum was founded in 1929 to gather and preserve the rapidly disappearing artifacts of America’s seafaring past. The museum grounds cover 19 acres on the Mystic River and include a recreated coastal village, a working shipyard, formal exhibit halls, and state-of-the-art artifact storage facilities.
“A stroll through the historic village enables visitors to experience firsthand from staff historians, storytellers, musicians, and craftspeople just what life was like to earn one’s living from the sea,” the museum says on its website. “In the Henry B. du Pont Preservation Shipyard, shipwrights can be observed keeping the skills and techniques of traditional shipbuilding alive as they restore and maintain the Museum’s watercraft collection and other vessels.”

The 41,000-square-foot Collections Research Center provides physical and electronic access to more than 2 million artifacts, ranging from marine paintings, scrimshaw, models, tools, ships plans, an oral history archive, extensive film and video recordings, and more than 1 million photographs —including what the museum labels “the incomparable Rosenfeld Collection.”
The research center also houses the G.W. Blunt White Library, a 75,000-volume research library where scholars from around the world come to study America’s maritime history.
Mystic is a village located in the towns of Groton and Stonington, Connecticut. It is about 105 miles north of Greenwich via CT-15N and I-95N.
5 More Connecticut Road Trips
- Groovin’ On Nature Road Trip
- Chow Down At ‘Birthplace Of The Hamburger’
- Go Round And Round In Bristol
- Fall In Love In Nature
- Road Trip Like Royalty
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