I have spent a lot of time in Connecticut. My wonderful aunt lives in Fairfield and my first memories of New York City are intertwined with her. We'd take Metro North to Grand Central and I never wanted to leave. Of course, now I long for more time in the "country."
My aunt is a great, healthy cook so I always crave her meals. But I love the Firehouse Deli and Isabelle et Vincent for amazing French bread. I've spent many hours at Jennings Beach, looking over the Long Island Sound.
Lyman Orchards: Somehow, I make it here at least once a year – usually for apples (and the best unsweetened applesauce in the world), pumpkins, kettle corn, and general fall merriment.
Branford & the Thimble Islands
This is a great summer day trip. Start 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 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 send new tours out every thirty minutes or so.
is a picture-perfect part of Connecticut, with enormous small-town charm and tree-lined streets. 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). Stop at Essex Coffee & Tea for a pick-me-up.
Drive from Old Saybrook (where Katharine Hepburn’s family had their summer home) to Madison, which is beautiful. Stop at Connecticut’s largest public beach, the massive Hammonasset State Park (there’s a parking fee Memorial Day through Labor Day), where you can enjoy a picnic lunch or enjoy two miles of beach, bike paths, and walking trails.
Madison & Guilford
These two adorable towns are quintessential Connecticut. One of my favorite small bookstores in the world is here, the beloved RJ Julia. Many of the books are adorned with handwritten staff recommendations. Inside the bookstore, RJ Cafe & Bistro is a great spot for lunch.
In Guilford, it feels like Gilmore Girls and Stars Hollow, the close-knit (but unfortunately fictional) town where the series is set. The Town Green is so beautiful. Stop at The Village Chocolatier for a sweet treat.