10 Ways to Enjoy a Summer Evening Last Updated 7/19

One of the things we love most about summertime in Connecticut is that long, purple, very pleasant period at the end of the day. The busy affairs of the daytime have come to an end, the midday heat is easing at last and it’s time for refreshment, maybe even a picnic, and a relaxing couple of hours as night so very gradually descends. Here are some good ways to spend your summer evening hours in Connecticut.

Drive-In Movie

There are still a few places in Connecticut where you can enjoy this throwback treat. Head to the Pleasant Valley Drive-In in Barkhamsted, the centrally located Southington Drive-In or the Mansfield Drive-In out east and you will experience the magic of dusk as it deepens around the big screen. It’s a great activity for kids who’ve never experienced it before.

Evening Concert

Music fills the air in Connecticut on summer evenings as towns and cultural organizations stage outdoor concerts all season long. One of the best series is the Hartford Symphony’s Talcott Mountain Music Festival in Simsbury, offering everything this summer from classical to pop to disco and the music of Queen. The Levitt Pavilion for the Performing Arts, from late June until the end of August offer over 50 free arts and entertainment under the stars and is located on the banks of the scenic Saugatuck River.

Up on the Roof

What is it about being up on a roof that’s so wonderful on a summer evening? We may not be able to describe it exactly, but we sure can experience it! Some of the places where you can give it a go are the spectacular Rooftop 120 in Glastonbury, Elbow Room in West Hartford, the new rooftop beer garden at Area Two by Two Roads Brewing Company and, the rooftop bar at Cava Restaurant in Southington. 

Poetry in a Garden

The Sunken Garden Poetry Festival at Farmington’s Hill-Stead Museum is one of Connecticut's great cultural treats. Attendees are encouraged to come early to tour the museum’s very fine Impressionist art collection (Monet, Manet, Cassatt, Whistler), walk the trails on the extensive grounds and picnic in the garden as the music and poetry take hold.

The Show of Swallows

This doesn’t happen until late summer, but the earlier you can reserve a space, the better. In late August and early September, a spectacular show of nature takes place at the mouth of the Connecticut River when as many as a half-million birds, mostly swallows, converge just before sunset over their roosting island. They create an extended ballet in the air before finally coming down to earth in what’s been described as a “funnel” or “rain.” Anyway, see it for yourself on the river (and probably never forget it) with the knowledgeable folks at Connecticut River Expeditions and their boat RiverQuest.

Hooked on Evening Fishing

Not that you can always believe a fisherman’s story, but many swear the fish bite harder and more frequently once the sun begins to go down. Whether you catch much or not, fishing from the shore is a wonderful way to enjoy summer’s long dusk hours. Check out a guide to some of Connecticut’s best spots on state-owned property along the shore, below.

The World’s a Summer Stage

Summer theater is a long-standing and wonderful tradition in Connecticut, and some of the theaters manage to retain the original informal, summery feel while putting together quality productions. The Summer Theatre of New Canaan is one of them, as are Musicals at Richter in Danbury and Sharon Playhouse in Sharon.

Comfortable Cruising

Float on Connecticut waters at twilight time, drink in hand, and life can seem but a dream. You can take in this summertime delight on the scenic Connecticut River, which takes on a special glow from aboard the riverboat Lady Katharine during their public cruises.

The Sycamore Scene

The Sycamore Drive-In in Bethel (est. 1948) was around long before the movie American Graffiti made drive-ins cool again, and its timeless charms are maybe best appreciated on a summer evening.  Get there on one of their Summer Cruise Nights and grab a burger and a homemade root beer. Prefer hot dogs? Go to Blackie’s in Cheshire (est. 1928) at dusk and feel the years peel back.