2021 Top 5 Fairs and Festivals in Connecticut

Many communities throughout Connecticut are excited to bring back festivals and fairs in 2021. Because Connecticut is small, traveling to quaint New England towns is both easy and rewarding. You’ll find plenty of events in New Haven, Guilford, and Southington. The close proximity of towns affords family and friends the ability to attend a variety of fairs and festivals within a 40-minute jaunt from Branford. From the shoreline to rural farmland, you’ll find interesting twists on food and entertainment in Southern Connecticut. We comprised our must attend list for 2021, and eagerly await the dates with baited breath.

North Haven Fair Food Festival

North Haven Fairground | May 26th 2021

Fair season is starting early this year with North Haven’s first annual Fair Food Festival! After missing out on some of your favorite fair foods in 2020, the North Haven Fair invites you to go outside and enjoy your favorite fare.

Indulge and enjoy favorites like fried dough, fresh-squeezed lemonade, fried Oreos, funnel cakes, pulled pork, and potatoes in daring forms! Don’t miss out on your favorite foods this year. Start a tradition and attend the first annual fair food festival! Learn more about the North Haven Fair Food Festival.

Midsummer Fantasy Renaissance Fair

Every weekend from June 26th to July 11th, 2021

Warsaw Park, 119 Pulaski Highway, Ansonia, Connecticut

The Midsummer Fantasy Faire is a unique and exciting way to step back in time sans unpredictable repercussions. Walk into a magical fantasy world set in medieval times. Enter a world from far away where elves, fairies, orcs, goblins, animal kin, dwarves, and magic are real. Go on a Shakespearan adventure, watch magical performances, and try various medieval foods from mead to turkey legs.

The Midsummer Fantasy Faire is one of the top renaissance festivals in Connecticut since 2011. Bring the entire family out to this event. You don’t want to miss it!

Travel to a far off world, the Midsummer Fantasy Faire by waving your hand.

Guilford Fair

Fairground of Historic Guilford | Sept. 17 – 19 2021

The Guilford Fair, presented by the Guilford Agricultural Society, is Connecticut’s 2nd oldest agricultural fair, established in 1859. This fair is held each year during the third weekend in September. Enjoy a variety of entertainment over the span of three days. This fair has paced with modern times yet remains the theme of the town’s agricultural past.

This family-friendly event has everything you can expect from a traditional fair with a variety of carnival rides, a petting zoo, hundreds of food vendors, and contests. The Guilford Fair is one of the largest fairs in New England. It’s no surprise it’s a local favorite! Read more about the Guilford Fair.

Southington Apple Harvest Festival

Southington Town Green | Oct. 1-3 | Oct 8-10, 2021

The 52nd annual apple festival in Southington, CT, is a 6-day event that takes place each fall. The apple festival draws in a crowd of over 100,000 people over the span of two weeks. This festival is one of the top tourist events in Connecticut. The Apple Harvest Festival is held during the height of New England’s beautiful fall foliage.

This festival is a food lover’s dream. You’ll find a variety of sweet apple desserts, from apple cider donuts to fried apple pie. This festival has become a tradition for many families in eastern Connecticut. The apple festival features live entertainment, arts and crafts vendors, hundreds of food vendors, carnival rides, and a fireworks display in the evening.

This is an event that you don’t want to miss! Learn more about the Southington Apple Harvest Festival.

Fantasy of Lights

Lighthouse Point Park in New Haven | Mid-November – December 31, 2021

The Fantasy of Lights is the perfect place to go to see a park filled with holiday light displays. With over 100,000 bulbs, the displays light up Lighthouse Point Park from late November until the end of the year. The Fantasy of Lights contains over 60 bright and colorful animated displays that captivate the holiday spirit.

Goodwill of Southern New England presents this yearly event. This event has become a holiday tradition for thousands of families. The Fantasy of Lights Festival is guaranteed to brighten up the holiday season with a nightly display of twinkling lights and music. Take a trip to Lighthouse Point Park in New Haven for a mile-long light spectacular. Learn more about the Fantasy of Lights.