The town green is as New England as unpredictable weather and Dunkin' Donuts coffee, and every Connecticut town - or nearly - has at least one of these grassy areas somewhere within its borders. Some of these greens resemble neglected yards, and others are so small they could be mistaken for traffic islands. The vast majority are pleasant, quiet spots featuring a few statues or war memorials and maybe a historic building or two. But a number of Connecticut's greens are true jewels, preserving centuries of history while thriving as gathering places for locals and attractive destinations for sightseers.
I could have chosen many different greens for this list, but I wanted to stick to the Connecticut Top Fives format, and to concentrate on a handful of very different town green experiences. If you travel to all of these greens, you'll find a distinct atmosphere at each one; if you only visit one, you'll still be pretty much guaranteed a trip that goes way beyond a nice walk in the park.
Guilford (The Pretty Green)
Guilford Green (pictured above) is simply, undeniably, one of those places that make you say "Ooh, pretty." Surrounded by churches, boutiques, historic houses, and eateries, it is the calm yet vibrant center of a completely adorable downtown. As you walk along the many pathways that divide the green, stop at each lamppost and read the small plaques printed with tidbits of Guilford Green-related trivia and history. Special events are held here regularly, but on a normal day the green is populated by people relaxing, working out, or simply navigating from, say, the sweet independent bookstore on one side to Town Hall on the other. Wander away from the green in any direction and you'll be rewarded with a choice of historic sites and endlessly photo-ready views in one of the Constitution State's most charming municipalities.
Guilford Green is bordered by Broad Street, Park Street, Whitfield Street, and Route 146.
New Haven (The City Green)
New Haven's green is one of the best-known examples of a town green that's grown up into a busy urban park. Today, looking at the open space where Yale students mix with tourists, men who seem to spend all day lounging on benches, and residents waiting for the bus, it's hard to imagine these 16 acres as a common area for grazing livestock. But if you can ignore the city noise (or perhaps imagine the cars as cattle?) you'll begin to see the green's past emerge. The historic churches, municipal buildings, and memorials on and around the green tell the stories of what came before. Or ignore the history and simply revel in the activity and diversity that would probably disturb the New Haven Colony's founders to no end. Today, the green is an all-purpose central meeting spot, hosting concerts and festivals. Located in downtown New Haven, it's also a good starting point for exploring the Yale campus or the city's numerous and acclaimed shops and restaurants or notable architecture.
New Haven Green is bordered by Church Street, Chapel Street, Elm Street, and College Street.
Lebanon (The Unspoiled Green)
The Lebanon Green is the closest you can get these days to seeing a town green as it was in ye olden dayes. This mile-long strip is more meadow than manicured lawn, because part of it is still used for agricultural purposes. (Time has moved on slightly in Lebanon, though - the green is no longer used for military drills.) In the summer, visitors strolling around the green can stop along the way at a collection of fascinating museums that explain why this now-sleepy town is so significant in American history. In a state with the slogan "Still Revolutionary," the town of Lebanon is as revolutionary as it gets, and that heritage all centers on the town green. (Don't be surprised if you see people dressed like it's 1781.) If you time your visit correctly, you can also catch the Lebanon Farmers' Market, one of my favorite of the many, many small Connecticut farmers' markets held on the local green.
Lebanon Green is bordered by West Town Street and Trumbull Highway (Route 87.)
Milford (The Long Green)
The emerald rectangle that is the Milford or Broad Street Green seems to go on forever, though it really only goes on for probably four or five (very long) blocks. (I wrote some more about the length of the green and other reasons to visit Milford last summer.) Because of its length and central location, this green has a bit of something for everyone. If you want a monument to look at, a bench to sit on, a place to grab lunch, or an old-fashioned gazebo, you'll find it here. You'll also find plenty of churches, banks, and other mundane institutions on the streets that border the green. Their presence is a reminder of the way the green blends seamlessly into everyday life in Milford. But retreat just a few steps off the sidewalk and onto the grass, and the everyday fades, revealing a sense of escape from the quick pace of this growing city. And when the green is taken over by an event like the annual Arts and Crafts Fair, the everyday disappears entirely, and the atmosphere becomes downright festive.
Broad Street Green is bordered by Broad Street and South Broad Street.
Tolland (The Small-Town Green)
When I first tried to think of the essential small-town green, a various greens kept floating through my mind, sometimes merging confusingly into a utopian town green composite. But as I pondered the question, I kept coming back to Tolland. Tolland's green has a traditional look, but it's also a little quirky. It's a little bit country, and simultaneously a little bit suburban. It always seems to be hosting events or preparing for various happenings whenever I drive past it. And although it feels very local, as if people might notice you're Not From Here if you stopped to get a closer look, it's also surrounded by enough eye-catching historic buildings that, if you explained why you stopped, the locals would surely understand and approve. Perhaps what makes Tolland's green stand out in my head is the way its attractions - like a preserved 18th century house that used to be a tavern and the Old Tolland County Jail and Museum - and even the roads leading up to it, like the Tolland Stage Road, hint at sedate rural Connecticut's intriguing past.
Tolland Green is bordered by Route 195, the Old Post Road, and Tolland Stage Road (Route 74.)