Driving the Connecticut Coast

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)

The Guilford Town Green has been a community gathering spot for hundreds of years.  (Photograph by Annie Fitzsimmons)
The Guilford Town Green has been a community gathering spot for hundreds of years. (Photograph by Annie Fitzsimmons)

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)

RJ Julia, a beloved small bookstore in a world of increasing online and e-book sales. (Photograph by Annie Fitzsimmons)
RJ Julia, a beloved small bookstore in a world of increasingly online sales. (Photograph by Annie Fitzsimmons)

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.

What are your favorite towns on the Connecticut coast? I always like to check out something new in when I’m in this beautiful state.


  1. Shoreline Expert
    CT Shoreline
    August 8, 2013, 12:01 am

    Chic’s is a staple childhood favorite, but all else Sue mentioned was only mentioned out of lack of experience. I grew up splitting time between Branford and Milford so I know both towns very well, Fairfield I’ve only spent a few days in. With that said–
    The beaches in Milford and West Haven might be larger and quit beautiful in their own right, but they don’t give you that same wonderful feeling as you take in the sites throughout Branford’s magnificently epic shoreline. Weather it’s the Thimbles or Kelsey’s Island off of Short Beach you really can’t go wrong. Names like Pine Orchard, Indian Neck, Pawson Park, Branford Point, and Stoney Creek will stand in my mind and heart as New England’s absolute gems. With respect to the other locations mentioned, the beaches a bit further north in towns like Branford, Guilford, Madison, and Clinton are classic New England. Gazing out into the water surrounding the Thimble Islands in Stoney Creek while the sun sets will with out any doubt touch your very soul while sites like Charles Island, West Haven Beach, and Silver Sands fall short. Sue, it’s a 20 minute ride, an hour before sunset; hope in the car, take a right off exit 56, and feel free to thank me when you get home.

  2. Rookie#1
    Rocheser NY
    June 18, 2013, 11:59 am

    The Connecticut coastline is enchanting and you missed some of the best parts, How about the shops in Essex, the little nook called Stoney Creek at the Thimbles, and of course the wonderful Southport Area? These are but a few of the treasures on the coast and of course then there is the slightly inland area Deep River etc.

  3. RK
    June 13, 2013, 2:54 pm

    Starting in Fairfield, it’d be a crime not to stop in Milford: the idyllic downtown complete with harbor, Silver Sands State Park and the boardwalk, and beautiful and historic Woodmont with stretches of both rocky and sandy beaches.

  4. Annie Fitzsimmons
    June 12, 2013, 10:20 am

    Hi Sue – All my CT trips start & end in Fairfield because that’s where I have family and have gone all my life. This two-day journey was really from Branford for the Thimble Islands to Essex and back up through Old Saybrook, Madison, and Guilford, ending with Bishop’s Orchards to pick up fruit & veggies. I love the beaches you mentioned but didn’t make it there on this particular trip. Thanks for the comment!

  5. Sue
    June 12, 2013, 9:21 am

    Am I missing something here? You talk about starting and ending in Fairfield but it seems like you are only covering Branford and eastern Ct. Nothing except a mention of Jennings beach in Fairfield. Seems you missed a lot of beach like Seaside Park in Bpt, Silver Sands State park in Milford and Long Wharf in. New Haven. And the beautiful beaches in West Haven and the great Boardwalk that takes you from Jimmies all the way past Chic’s. What route are you taking? Maybe it’s the mobile coverage on my phone missing links to details but this story needs some more info.

  6. wendy
    Guilford, CT
    June 12, 2013, 8:48 am

    And don’t forget to stop by M!X Design Store on the beautiful Guilford Green (www.mixdesignstore.com)

  7. Melissa Calkins
    Formerly of Niantic, CT
    June 11, 2013, 10:29 pm

    Your travels should have started at Stonington through Mystic, New London, Waterford, Niantic, Old Lyme to Saybrook….so many beautiful areas missed!

  8. Chris
    June 10, 2013, 8:07 am

    What about Clinton?I grew up here and it has a rich historical past,as well as having the distinction of being where Yale started.Plus,it’s just as wonderful as any other shoreline town you mentioned.

  9. Bryan ens
    North haven,ct
    June 9, 2013, 11:31 am

    You missed ctbiketours.com! It’s a 4 hour bike ride along the Bradford/guilford coast. Absolutely beautiful and it was a great way to see the area. I highly recommend it! He combines it with a boat roar of the islands as well, a real treat!