From lobster rolls to garlic, pumpkins to Irish tunes, Connecticut’s Sept. 18–21 weekend is packed with food and festivals.
CONNECTICUT — The Nutmeg State is diving headfirst into fall fun this weekend with a lineup that’s as flavorful as it is festive. From lobster rolls on the shoreline to garlic-inspired dishes in Mystic, plus boat shows, art fairs, and pumpkin celebrations, Sept. 18–21 offers a little something for everyone. Whether you’re a foodie, a festival lover, or just looking for a good old-fashioned country fair, the Connecticut has you covered.
Seafood lovers, rejoice! On Saturday, Sept. 20, downtown Milford hosts its first Regional Lobster Roll Festival. Expect buttery lobster rolls galore, plus live music, beer tents, and vendors serving up coastal favorites. It’s the perfect chance to savor a classic New England bite while strolling along the historic Green.
Running Sept. 19–21, the Guilford Fair is one of Connecticut’s most beloved fall traditions. With midway rides, farm animal exhibits, live music, and plenty of fair food, it’s a full weekend of family fun. This year’s entertainment lineup includes national touring acts and local favorites, making it a true community celebration.
Mystic gets extra aromatic Sept. 20–21 during the Garlic Festival, where vendors highlight the bulb in every possible form—garlic bread, garlic dips, garlic-infused oils, even garlic ice cream. Along with the food, expect live music, cooking demos, and family activities. Just don’t forget the breath mints.
If the sea is calling, head to the Norwalk Boat Show at Norwalk Cove Marina, Sept. 18–21. The show features more than 300 boats, from luxury yachts to fishing vessels, along with interactive exhibits, paddleboarding, and kids’ activities. It’s the ultimate weekend on the water for boating enthusiasts. Tickets here.
Back in Milford, shamrocks and fiddles take center stage during the Milford Irish Festival, Sept. 19–20. With live Celtic music, step dancing, cultural exhibits, and plenty of Irish food and beer, it’s a lively celebration of Irish heritage on the Green.
On Sunday, Sept. 21, the Seymour Pumpkin Festival returns with its family-friendly mix of pumpkin decorating, craft vendors, live music, and seasonal treats. It’s the perfect way to kick off autumn while supporting local nonprofits.
From Sept. 18–20, the Holy Trinity Greek Festival in Norwich offers traditional Greek cuisine, music, and dancing. Enjoy gyros, souvlaki, baklava, and more while taking in authentic cultural performances.
Nature lovers can spend Sunday, Sept. 21, at Butterflies, Birds & Blossoms, presented by the Catherine Violet Hubbard Animal Sanctuary in Newtown. The day features butterfly releases, bird demonstrations, and garden tours — not to mention adoptable pets.
Finally, art takes center stage at Sharon Green with the Voice of Art’s Fine Art Festival (Sept. 20–21). The juried show brings together regional artists showcasing painting, sculpture, photography, and mixed media. The setting on the historic Green makes it one of the most scenic art fairs of the season.
From garlic to gyros, lobster rolls to pumpkin spice, Connecticut is serving up a weekend full of flavor and festivity. Whether you’re on the shoreline, in the hills, or strolling through a town Green, you’ll find plenty of reasons to celebrate the season.