10 Best Outdoor Festivals in Connecticut

10 Best Outdoor Festivals in Connecticut

If you’re looking for some like-minded folks to enjoy all of the awesome outdoor beauty Connecticut has to offer, why not hit one of the state’s fantastic outdoor festivals? Whether running, biking, sailing, paddling or skillet throwing is your thing, you’re sure to find a festival that will be fun for you. Take a look at our favorite outdoor festivals in Connecticut.

1. Sailfest, New London, CT

At Sailfest, in New London, you’ll be able to enjoy all that a seaside summer festival has to offer, from fireworks and live music to food and rides. Launch your sloop and set sail among the tall ships that will be on hand in the harbor or don your running shoes and hit the road in the Charter Oak Federal Credit Union 5K Road Race. Then cool off at the beer tent. Mashantucket Pequot Tribal Nation, The Day, 100.9 K Hits, and many more sponsor this year’s event.

2. Dragon Boat & Asian Festival, Hartford, CT

The annual Dragon Boat and Asian Festival takes place every summer on the Connecticut River in Hartford. Join a team or start your own, then practice paddling and show off your skills at the festival, which is also a celebration of Asian culture. Off the water, you’ll find food, demonstrations and much merriment as you regain the feeling in your arms. Sponsors like Travelers, Greater Hartford Arts Council , Stanley Black & Decker make this festival possible.

3. Mohegan Wigwam Festival, Uncasville, CT

The Mohegan Wigwam Festival is an opportunity to immerse yourself in the culture of one of the peoples who have called Connecticut home the longest: The Mohegan Tribe. Native food and craft vendors will be on hand, but the highlight of the festival is the Native dance competitions, featuring dancers in full tribal and ceremonial regalia.

4. Milford Oyster Festival, Milford, CT

One of the state’s premier annual food parties is the Milford Oyster Festival, which boasts more types of oysters than you’ll find at any other festival in the country. In addition to eating oysters, you can hit the high seas on a tall ship schooner or under your own power during the annual canoe and kayak races. Then quench your thirst with a beverage from local brewers such as Two Roads and Half Full Brewery at the craft beer and wine garden. The East Coast Shellfish Growers Association, The Big Bite Tour , Star 99.9 and many more are partners for this year’s event.

5. Connecticut Maritime Heritage Festival, New London, CT

Connecticut is a state with a long maritime tradition, and each year folks celebrate with the Connecticut Maritime Heritage Festival. Apart from visiting tall ships and watching them race, festival goers will enjoy food and entertainment, as well as seminars on topics such as maritime careers and a Coast Guard search and rescue demonstration. Other activities include dance lessons and a family fishing tournament. Connecticut Municipal Electric Energy Cooperative, The Gallery at Firehouse Square, and Xfinity bring you this year’s amazing event!

6. Four Town Fair, Somers, CT

The Four Town Fair in Somers traces its history back nearly 200 years, making it one of the oldest such festivals in New England, if not the country. In addition to the food, entertainment and events that you would expect at small-town fair, like goat showmanship and working oxen, there are plenty of events that goatless and oxenless folks can get in on, as well. For example, you could jump in on the skillet throw, show off your drawing skills, or offer up your expertise in a pie or corn eating contest. Fine folks like Lori Spielman Landscaping and Harvest New England keep the Four Town Fair going strong.

7. Hartford Marathon, Hartford, CT

The Eversource Hartford Marathon is about way more than 26.2 miles on an October Saturday. There’s a festive celebration with live music, beer and food. There’s also a half-marathon, a charity 5K, a kids run and even a team-relay marathon if you want the 26.2 bragging rights but don’t want to do it all by yourself. Cyclists can hit the road early and bike the closed marathon route before start time as part of Pedal to the Medal. United Bank, Hartford Hospital, and nuun are some of the marathon’s partners this year. 

8. Apple Harvest Festival, Glastonbury, CT

One of Connecticut’s favorite fall events, Glastonbury’s Apple Harvest Festival brings with it bushels of fun and activities for folks of all ages. You got your live music and your midway rides. But you’ll also get food trucks, the Harvest Pub and the pie tent. You can run off all that beer and pie at the Angry Orchard Apple Festival 5K.

9. No Child Left Inside Winter Festival, Torrington, CT

For more than a decade, the Department of Energy and Environmental Protection (DEEP) has hosted the No Child Left Inside Winter Festival. The festival is extremely family-family friendly and is designed to get people into the great outdoors during the depths of winter. You’ll find all sorts of activities from snowshoeing to ice sculpting, winter hikes to ice fishing. There will be an ice safety demo by the Torrington Fire Department, bonfire, fish fry and marshmallow roast—all outside. Sponsors include the likes of L.L. Bean and Bass Pro Shops

10. Shad Derby Festival, Windsor, CT

There is probably no fish or fishing event in Connecticut that is more popular than the annual Shad Derby Festival in Windsor. There are so many events that it would probably be impossible to do them all. A bowling tournament, fishing tournaments—for kids and adults—a golf tournament, road races, beer tasting, bingo… even a basketball skills competition and a blood drive. You will not be bored if you choose to do the Derby. Sponsors include Mitchell Selig Ford, Konica Minolta, and Windsor Federal Savings.