I seem to gravitate toward nostalgia-driven travel in the summertime.
Standing on Jennings Beach and gazing out on the Long Island Sound makes me feel like I’m 12 again. Time just seems to stand still in Fairfield. I have been coming to this beach in this idyllic small town with my aunt Carol for as long as I remember. But we’d always spend time in New York City together first. We’d squeeze as much into one day in the city and then spend the rest of our time exploring Fairfield and its environs. All I wanted then was to follow the signs to Manhattan. But now that I live in the city, I long for more time in Connecticut. The grass is always greener, right?
I can remember the first time I drove to Connecticut by myself. Newly 16, I had been given the keys to my first car, Dad’s green Buick LeSabre, otherwise known as “Chunks” (I think every car should have a name). Chunks and I would go on to criss-cross the country together, but I will never forget my first solo drive up the Connecticut coast and the freedom of striking out on my own with the window down.
Whether or not you have ties to Connecticut, the drive along its shoreline is one of the most scenic byways in America.
For an ideal weekend trip, follow my route through some of Connecticut’s most charming towns on a loop from Fairfield to Essex and back:
Day 1 (Fairfield to Essex)
Start your journey right with a lobster roll at the Lobster Shack in Branford at a picnic table that overlooks boats on the river. You won’t find any mayo on a Connecticut-style roll — just melted butter and a squeeze of lemon over fresh lobster on a toasted bun.
Branford is the jumping off point for your afternoon activity: a narrated boat tour of the Thimble Islands. You’ll see where circus performer Tom Thumb visited his lady love, President William Howard Taft’s short-lived summer White House, and a host of glorious Victorian houses as you flit between these privately owned islands. There are three boat companies (I opted for Captain Bob’s), all of which seem to send new tours out every half hour or so.
From Branford, follow I-95 north to Route 9. Just up the road you’ll enter Essex, your picture-perfect home for the night. Located on the banks of the Connecticut River, Essex has a rich history and small-town charm with tree-lined streets and American flags waving. I fell in love with the Griswold Inn because it authentically embodies colonial New England, while serving up delicious comfort food and live music in the Tap Room (make sure to stop into the Goods & Curiosities shop for fun gifts). After a quick spin around the Connecticut River Museum, you’ll face the hardest decision of your trip: whether to have chocolate or cinnamon on your cappuccino at Essex Coffee & Tea.
Day 2 (Essex to Fairfield)
The stretch from Old Saybrook (where Katharine Hepburn’s family had their summer home) to Madison is my favorite part of the drive. Stop at Connecticut’s largest public beach, the massive Hammonasset State Park (there’s a $9 parking fee Memorial Day-Labor Day), where you can enjoy a picnic lunch or enjoy two miles of beach, bike paths, and walking trails. Madison boasts one of my favorite small bookstores in the world, the beloved RJ Julia. Many of the books are adorned with handwritten staff recommendations and, if you’re anything like me, you’ll leave with a stack of new finds. Inside the bookstore, RJ Cafe & Bistro is a great spot for lunch.
From Madison, head to Guilford. If you’ve ever seen Gilmore Girls, you may feel like you’ve stumbled upon Stars Hollow, the close-knit (but fictional) town where the series is set. Head to the Town Green, a community focal point that plays host to graduations, festivals, and parades. Walk a few blocks and you’ll find several historic house museums including the Henry Whitfield House, Connecticut’s oldest home. If you’re sticking around for dinner, try Guilford Mooring or Guilford Lobster Pound in the harbor for outdoor dining on the docks. Regardless of how long you stay, make sure to stop in for a caramel or another classic sweet at The Village Chocolatier before you hit the road again.