Connecticut

Top 10 Connecticut Summer Events of 2020

From jazz in the Litchfield Hills to a craft expo on a historic town green, our list of the 10 best Connecticut summer events has something for everyone.

By Yankee Magazine

Apr 06 2020

Top-10-Connecticut-Summer-Events

Performances on the New Haven Green are among the highlights of the annual International Festival of Arts & Ideas.

Photo Credit : International Festival of Arts & Ideas
EDITORS’ NOTE: The nation is still dealing with COVID-19 at the time of this post, meaning it’s not known whether the 2020 dates for these events are confirmed. We’re hoping for the best, but please check with organizers before making your summer travel plans! 
From jazz in the Litchfield Hills to a craft expo on a historic town green, our list of the top 10 Connecticut summer events has something for everyone. Read on to see our picks, then tell us about your own favorite Connecticut summer events in the comments!
Performances on the New Haven Green are among the highlights of the annual International Festival of Arts & Ideas.
Performances on the New Haven Green are among the highlights of the annual International Festival of Arts & Ideas, one of our favorite Connecticut summer events.
Photo Credit : International Festival of Arts & Ideas

Top 10 Connecticut Summer Events of 2020

Sea Music Festival Mystic | June 11–14, 2020

More than 5,000 people gather at Mystic Seaport each year to hear performers perform maritime music ranging from the golden age of sail to the best of contemporary compositions. There will be not just concerts but also workshops and special kids’ performances. Daytime concerts and workshops are open to all museum visitors; however, evening concerts require separate tickets. SEE MORE:Mystic Seaport | Maritime History in Connecticut

International Festival of Arts & Ideas New Haven | June 13–27, 2020

Held at various locations throughout New Haven but centered on the Yale campus and the historic New Haven Green, this mix of dance, music, theater, and engaging speakers boasts more than 170 events — almost 85 percent of which are free. SEE MORE:Things to Do in New Haven, CT | Where Food and Culture are Ivy League

Norfolk Chamber Music Festival Norfolk | June 15–August 15, 2020

Born from the local Battell family’s tradition of hosting summer concerts on the Norfolk town green back in the 1880s, this festival today is run by the Yale University School of Music and located on the genteel estate of a Battell descendant. Each summer it welcomes emerging and world-class artists and ensembles for a series of 30-plus performances and events. [text_ad]

Sailfest New London | July 10–12, 2020

Considered southeastern Connecticut’s premier summertime event, Sailfest draws more than 300,000 visitors to the New London waterfront district for free entertainment on two stages, 200-plus food and craft vendors, amusement rides, and a major fireworks show. To take in the festivities from the water, you can buy a ticket for a harbor cruise aboard the tall ship Mystic Whaler, a reproduction of a late-19th-century cargo schooner. SEE MORE:New London, New Hampshire | Could You Live Here?

Craft Expo Guilford | July 17–19, 2020

The Guilford Art Center’s annual Craft Expo returns to historic Guilford Green, bringing with it some 180 nationally recognized artisans. Almost every conceivable medium is represented — ceramics, fiber, glass, leather, metal, painting, and photography, among others — and all of the items on display and offered for sale are handmade. Browsers can revive themselves at a food court (with beer and wine), while parents will appreciate the family art tent and its craft activities for youngsters.

Litchfield Jazz Fest Goshen | July 25–26, 2020

Set against the picturesque backdrop of the Litchfield Hills, this jazz fest got under way in 1996 with a lineup that any well-established festival would envy today (e.g., Diana Krall, Christian McBride, and Terence Blanchard). The event continues to spotlight up-and-coming talent. SEE MORE:Fall Comes to Connecticut’s Litchfield Hills

Holy Rosary Italian FestivalAnsonia | August 6–8, 2020

It’s “Festa” time in Ansonia, and that means a varied assortment of mouthwatering foods — lasagna, fried calamari, sofritto, zeppole, gelato, pastries — plus midway rides and games of chance, live music, and a cash raffle, all within the family-friendly atmosphere of the Holy Rosary Church grounds.

Mystic Outdoor Art Festival Mystic | August 8–9, 2020

The oldest event of its kind in the Northeast, the Mystic Outdoor Art Festival attracts more than 85,000 people from around New England and beyond to Mystic, Connecticut, with its lineup of 250 juried artists. All told, there’s more than two miles’ worth of arts and crafts booths to peruse, with the artwork spanning oils, watercolors, and pastels to photographs, sculpture, and woodwork. This free festival offers activities for all ages to enjoy, including a children’s “art park,” plus food and drink for sale by local charitable organizations. SEE MORE: Mystic, Connecticut | Could You Live Here?

Brooklyn Fair Brooklyn | August 27–30, 2020

First held in 1809, the Brooklyn Fair is among the oldest continuously running agricultural fairs in the U.S. and one of our favorite Connecticut summer events. But it’s aged quite nicely: Musical headliners have included the likes of top-selling national artists Collin Raye and Lady Antebellum, while the carnival midway seems to grow bigger every year. And of course there are all the things we love about country fairs, including pig races, tractor pulls, an arm wrestling contest, and the chance to see plenty of blue-ribbon livestock up close. SEE MORE:Guide to the Biggest Agricultural Fairs in New England

Oyster Festival East Norwalk | September 11–13, 2020

Norwalk gives thanks for its maritime bounty at this venerable seafood bash, which has grown from 10,000 attendees in 1978 to more than 60,000 today. Oysters play a starring role both in the food court (which has plenty of other seafood and non-seafood options, too) and in events like the oyster slurping contest. Look for a full array of amusement rides, including a 65-foot gondola Ferris wheel, alongside live music and entertainment such as the Paul Bunyan Lumberjack Show; harbor cruises; and displays of oyster history and artifacts.  What are your favorite Connecticut summer events? Let us know! This post was first published in 2017 and has been updated.

SEE MORE: Top 10 Rhode Island Summer EventsBest Connecticut Coastal TownsLobster Landing | The Best Lobster Roll in CT?