Simsbury Celebrates: Each year on the Saturday after Thanksgiving from 4 to 8:30 p.m.  Simsbury turns the “main drag” (Hopmeadow Street) into a walking mall of entertainment. Numerous family-friendly acts and activities are available for free, capped by a fantastic fireworks display at the Performing Arts Center. For information on this event, go to

Martin Luther King Jr. Day:  An annual observance in January at the First Church of Christ organized by the MLK in Simsbury Celebration Committee to mark the town’s special relationship to Dr. King. The two summers King spent on Simsbury tobacco farms were instrumental in shaping his personal philosophy, his decision to become a minister and where he first experienced racial integration.

Simsbury Triathlon Race - Third Sunday in May: The Triathlon starts with a 3.6-mile “River to Ridge” running/hiking segment from the banks of Farmington River up through Penwood Forest, loops around a lake on the Metacomet Trail and back down to the river. Next is an 11.5-mile bicycling course, comprising two loops on country roads and a short piece on the Farmington Valley Greenway. In lieu of swimming, the final component is a two-mile loop on the Farmington River – paddling upstream first and then back, crossing twice under Simsbury’s landmark Old Drake Hill Flower Bridge. The race should take approximately two hours for most racers. For more information go to

Memorial Day Parades: Parades are held each Memorial Day at 9 a.m. in Tariffville and also at 1 p.m. on Hopmeadow Street in downtown Simsbury.

Iron Horse Half Marathon early every June: The Hartford Marathon Foundation schedules an annual half marathon beginning and ending in the center of Simsbury. Runners will enjoy the picturesque course along the Farmington River and the farmlands of Simsbury. Events include a 10K, 5K and Half.

Simsbury Maker Faire

Maker Faire is a gathering of fascinating, curious people who enjoy learning and who love sharing what they can do. From engineers to artists to scientists to crafters, Maker Faire is a venue for these “makers” to show hobbies, experiments, projects. At the Library and adjacent grounds, Makers of all types will gather in Simsbury for a family-friendly showcase of invention, creativity and resourcefulness — a celebration of the Maker movement. Visit for more info.

The Simsbury Mini Maker Faire is presented by the Simsbury Public Library in partnership with the Simsbury Main Street Partnership. The Simsbury Mini Maker Faire is independently organized and operated under license from Maker

Iron Horse Car Show: The Valley Collector Car Club car show is an annual event to benefit local charities on the second Sunday in July. The cars are displayed on Iron Horse Boulevard in downtown Simsbury from 10 a.m. to 3 p.m. Donations are suggested. Parking is at Simsbury Meadows.

The Jamie McEwan Whitewater Triple Crown Kayak Races: The whitewater triple crown is a competition in Tariffville Gorge for kayakers and canoeists in the three major whitewater disciplines: Wild water racing is about speed; the fastest boat down the river wins. Slalom requires precision. The paddlers must negotiate a series of gates for the fastest time. Freestyle is an acrobatic contest of spins, cartwheels and flips in whitewater. Incredible balance and reflexes prevail as paddlers are judged for their tricks. The competition can be seen from the banks of the river on both Saturday and Sunday on a weekend in spring or summer depending on river levels. For information on when and where to watch this impressive event, go to

The Taste in Simsbury: A gourmet food festival where you can sample the specialties of the best area restaurants as well as beer, wine and desserts all in one place! It’s held every August in Simsbury.

Septemberfest: The annual three-day festival on the first non-holiday weekend in September, is a fundraiser for the Simsbury Performing Arts Center with entertainment for all ages. The band shell features live music, kids enjoy bounce houses, train rides, games, story tellers, puppets, hot air balloon rides and more. Food and drink is provided by local restaurants. Friday night features fireworks. Admission and parking on the grounds is free.

Simsbury Giant Used Book Sale:  Early every September, Simsbury hosts a colossal used book sale attracting book dealers from all over the northeast at Simsbury High School, at 34 Farms Village Road (Rte. 309). Hundreds of thousands of used books are sold each year, most for under $1.50 each. The sale is both Saturday and Sunday. If you are a reader, this shouldn’t be missed!

Contact Simsbury Public Library for more information:


The Simsbury Fly-In & Car Show: The Fly-In & Car Show at Simsbury Airport on Wolcott Road is held on a Saturday every September and is always a great event. There are, of course, lots of small aircraft to see, both doing aerial tricks and on the ground. There are loads of antique cars. There are exhibits, performances and seminars. And there is food and drink!, 860-693-4550.

Annual Arts & Crafts Festival: The Simsbury Woman’s Club hosts an Annual Arts and Crafts Festival each September. Over 100 artists and craftsmen exhibit on Iron Horse Boulevard in Simsbury Center from 10 a.m. to 5 p.m. on a Saturday and Sunday. Admission and parking are free. Demonstrations, food and a bake sale are included. Proceeds go to charity. For more information please contact the Woman’s Club at

Classic Horse Show: Every September at Folly Farm, the Classic features top horses and riders from earlier competitions. It starts at 8 a.m. and ends at dusk and has lots of family-friendly non-horse fall activities.

Heublein Tower Toot: Scheduled every year to coincide with peak fall foliage viewing, Heublein Tower’s Annual Tower Toot in Talcott Mountain State Park is held on a mid-October weekend. Hike to the Tower and enjoy refreshments, games for children, face painting, visits, tours of the Tower and live music. Admission is free.

Simsbury Spooktacular Chili Challenge: Sponsored by the Simsbury Chamber of Commerce, it is an annual event held on the last Saturday of October.  The event includes live entertainment, trick-or-treating for the kids, a costume contest, and a chili cook-off competition sanctioned by the International Chili Society (ICS).

Simsbury, CT Foliage Tour #1
Tour #1 starts at Rosedale Farm, 25 East Weatogue Street and ends in the center of town. It is approximately 13 miles. See route details here.