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(Photo courtesy of Katy’s Courage)

Sometimes, the best way to explore the South Fork and Shelter Island is by foot. That wasn’t a traffic joke. As the weather heats up, so does the annual road racing season. 

Think of it as a way to choose your adventure. There are quick 5Ks that’ll give you an endorphin-induced jolt that rivals your Hamptons Coffee order (and some even end with a different kind of local celebratory brew!). And then there’s the annual Hamptons Marathon for those looking to break through the wall (if you know, you know).

From triathlons to fun runs, you can hit the ground running by signing up for one of these 2023 Hamptons road races.

Katy’s Courage 5K

When: Saturday, April 22, 8:30 a.m.

Where: 21 West Water St., Sag Harbor Village

Cost: $25 in advance, $30 day of

What to know: This quick run is the perfect excuse to dust off your running shoes and any rusty bits you developed during the winter. The historic Main Street is included in the route. Funds go to local scholarships and Katy’s Kids @ CMEE, which helps children, teens and their families grieve the loss of a loved one. Register here.

Westhampton Beach Brewing Company Riptide Run 5K

When: Saturday, April 22, 10:30 a.m.

Where: 7 Glovers Lane, Westhampton Beach

Cost: $60 (run and post-race party), $40 (run and non-alcoholic beverages at the post-race party)
What to know: This 5K coincides with the town’s Spring Fling Festival. Let it rip in a 5K and toast to your time — whatever it is — with Westhampton Beach Brewing Company, which will have a beer tent for two hours. The family-friendly affair also includes discounts for people under 21 and designated drivers, plus petting zoos, live music and games. Register here.

Bridgehampton Half Marathon & 5K

When: Saturday, May 6, 9 a.m. (half), 9:15 a.m. (5K)

Where: End of the Beebe Windmill, Bridgehampton

Cost: $95 in advance (half), $100 day of (half), $40 through 5/1 (5K), $45 after 5/1 (5K)

What to know: Though the half marathon is 10 miles longer, both flat and fast courses will take you through Sagaponack and Bridgehampton and include bucolic views of horses and potato farms. Everyone doesn’t get a trophy, but all participants do get a swag bag. Register here.

May Day 5K Run

When: Sunday, May 7, 9 a.m. 
Where: Main Beach at 101 Ocean Ave, East Hampton

Cost: $30 in advance, $35 day of

What to know: This annual 5K at Main Beach honors Mental Health Awareness Month by donating proceeds to the Tyler Project, a non-profit committed to bringing concerns about mental health and cyberbullying in teens and young adults to the forefront of public consciousness. The first 700 people to sign up get a T-shirt. Register here. 

RJ Aaron Memorial Mighty Montauk Triathlon

When: Saturday, June 10, 7:30 a.m.

Where: Starts at Lake Montauk, finishes at Triangle of Star Island Road and West Lake Drive

Cost: $35 until June 6, $150 from June 7-9

What to know: This late-spring tradition at The End began in 1982. It includes a one-mile swim in the serene Lake Montauk, a 20-mile bike ride that includes a view of the Montauk Lighthouse from above and a not-for-the-faint-of-heart 6.2-mile picturesque run through The End’s famous hills. Real talk: The course has to be completed in 3 hours and 55 minutes — it’s not for beginners. Proceeds go toward LI-based beneficiaries like the Lustgarten Foundation for Pancreatic Cancer Research and the St. Terese Youth Group. Register here.

The start of the annual Shelter Island 10k. (Photo credit: Julie Lane)

Montauk Mile

When: Sunday, June 11, 10:30 a.m. (women), 11 a.m. (men)

Where: Lion’s Field (South Erie and Edgemere Street), Montauk

Cost: $30 in advance, $35 day of

What to know: Go the extra mile to help the East Hampton boys and girls varsity cross country team raise money to race in a competitive meet this fall. Register here.

Beacon of Hope 5K

When: Saturday, June 17, 9 a.m.

Where: 2000 Montauk Highway, Montauk

Cost: $30 until May 17, $35 from May 18-June 16, $40 day of

What to know: This course will take you through Camp Hero and finish at the iconic lighthouse. Proceeds benefit East End cancer organizations Lucia’s Angels and the Coalition for Women’s CancersRegister here.

Shelter Island 10K & 5K

When: Saturday, June 17, 5:30 p.m. (10K), 5:50 p.m. (5K)

Where: 33 N Ferry Road, Shelter Island

Cost: $45 in advance (10K), $45 day of (10K), $35 in advance (5K), $40 day of (5K)

What to know: The annual race around the Island is a runner’s favorite, as much for the roadside resident cheering, as for the multiple pitstops with water, often handed out by the island’s youngest residents. You might even be handed an adult beverage or two along the route (hey, it’s after 5:00—that’s how they roll on the rock). Register here.

Ellen’s Run

When: Saturday, Aug. 20, 9 a.m.

Where: Southampton Intermediate School, 70 Leland Lane, Southampton

Cost: TBD

What to know: The 28th annual 5K benefits the Ellen Hermanson Foundation, whose namesake was a breast cancer warrior who died in 1995. Register here.

Hamptons Marathon & Half Marathon & 5K

When: Sept. 23, 2023, 8 a.m. (marathon/half), 8:15 a.m. (5K)

Where: Southampton Intermediate School, 70 Leland Lane, Southampton

Cost: $100 through July 10 (marathon), $110 through Aug. 7 (marathon), $120 through Sept. 11 (marathon), $125 after (marathon), $85 through July 10 (half), $95 through Aug. 7 (half), $105 through Sept. 11 (half), $100 after Sept. 11 (half), $40 through Sept. 11 (5K), $45 after Sept. 11 (5K)

What to know: People spend all summer training for this annual goal race. The pre-pandemic 2019 version featured competitors from 40 states and 14 countries. The run starts in Southampton and includes a range of scenery, from woodland to the Atlantic Ocean and Shinnecock Bay. The marathon is a Boston qualifier.