Get the whole family together for a fun run this September or October, from Darien’s own race at Pear Tree Point Beach to a fun run at the SoNo Half Marathon.

Darien Road Race

When: Sunday, September 15, 2024; 1.5 mile fun run at 9am, 5-mile race at 9:30am, beachside family fun activities 8am-11am

Where: Pear Tree Point Beach, Darien

Why: Always a favorite hometown event, this race raises funds for The Community Fund of Darien, which supports 35 local nonprofits such as Inspirica, Kids in Crisis, The Depot, Star Inc, Boys & Girls Club of Stamford and more.

Sign Up: Register here, $50 per adult, $25 for ages 6-18 and kids 5 and under are free.

Pequot Runners Kids Only Race

When: Sunday, September 22, 2024; 9:30am

Where: Greens Farms Academy, Westport

Why: This race, put on by the Pequot Runners, is just for kids! Two races, broken up by age are held and each race is capped at 75 kids. 4th-5th graders will run 1.5 miles and 6th-8th graders will run 2 miles.

Sign Up: Register here, $25

Bigelow Tea Community Challenge

When: Sunday, September 29, 2024; kids fun run at 9am, 5k at 10:10am, 3k walk at 10:10am.

Where: Wakeman’s Boys and Girls Club, Southport

Why: Last year, the race raised over $155,000 for Bridgeport/Fairfield based charities. The fun run, for kids ages 10 and under, includes a 100-yard scamper, 1-mile jog and an obstacle course along with awards, snacks and fun activities.

Sign Up: Register here, $15 kids fun run, $40 5k run, $38 3k walk.

SoNo Half Marathon

When: Sunday, October 6, 2024; half marathon at 8:30am, 5k at 8:35am, kids fun at 11:30am

Where: Veteran’s Park, Norwalk

Why: All the excitement of a half marathon, with a totally doable kids fun run that includes medallions for all finishers. A big post race party includes free pizza, cookies, fruit and ice cream. This event sells out, so be sure to book early.

Sign Up: Register here, kids race is free, 5k $45 adults and $40 kids, half marathon $85 adults and $80 for kids, all fees waived with a $250 fundraiser minimum.