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The 8th annual race-of Hope in Southampton August 7, 2023. (Photo by Sean Zanni/PMC)

That spring in your step? It’s real. Warmer weather may have you walking lighter and motivated to get outside and grow as you go for a goal. Signing up for a road race in the Hamptons offers a chance to do both. The South Fork and Shelter Island road-racing calendar gears up in April, and summer weekends offer options aplenty. The various distances — 5K to the always-anticipated Hamptons marathon — allow people to reach a goal that works for them. What’s more, it’s a chance to see friends and neighbors you haven’t seen since your town’s tree and Menorah lighting (to be fair, it’s been rather cold). Many community races donate proceeds to a good cause, too, meaning the registration fee truly goes the distance.

Whether you’re training for your 10th half marathon or first-ever 5K, all roads lead to a start line at these Hamptons road races in 2024.  

Katy’s Courage 5K

When: Saturday, April 13, 8:30 a.m.

Where: Water Street, Sag Harbor

Cost: $25 in advance, $30 day of

What to Know: Always one of the first races on the Hamptons calendar, this fast, flat 5K will once again continue to support local scholarships. This year, proceeds will also go toward a new partnership with CMEE: Katy’s Kids @ CMEE Center for Grieving Children and Their Families, which aims to provide chances to play and receive expressive peer support for grief and loss.

Westhampton Beach Brewery Riptide Run

When: Saturday, April 27, 11 a.m. (Rain date Sunday, April 28)

Where: 7 Glovers Lane, Westhampton Beach

Cost: $60 (5K and party), $40 (5K only) and $40 (Party only, 21+)

What to Know: Finish lines are easier to find when there’s a brew waiting for you. West Hampton Beach Brewery’s annual Riptide Run includes a 5K and after-party for those of legal age. Running can be a family affair, though. A fun run for future jogger Joes kicks off shortly before the 5K at 10:30 a.m.

OMAC May Day 5K

When: Sunday, May 7, 9 a.m.

Where: Main Beach, East Hampton

Cost: $30

What to Know: Run with a view of Main Beach while supporting the Tyler Project, which is dedicated to mental health awareness.

Mr. Long See You Out There 5K Run/Walk

When: Sunday, May 18, 9 a.m.

Where: 6 Central Ave., East Quogue

Cost: $30

What to Know: This annual race provides scholarships in Rob Long’s name to East Quogue Elementary School graduates.

RJ Aaron Memorial Mighty Montauk Triathlon

When: Saturday, June 8, 7:30 a.m.

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

Cost: $150 before May 26, $160 until June 6

What to Know: Swim for a mile, bike for 20 and finish with a 10K run at this 42-year-old tradition that takes people through Montauk. Proceeds go to various organizations, including the Lustgarten Foundation for Pancreatic Cancer Research and the East Hampton PBA.

Montauk Mile

When: Sunday, June 9, 10:30 a.m. (men), 11 a.m. (women)

Where: Lion’s Field, Montauk

Cost: $30

What to Know: Tack on a mile to your triathlon or consider yourself inspired by those who dared to try the day before with this mile-long race. Bonus: The first 100 people to sign up get a commemorative pint glass to toast with at the finish line.

Beacon of Hope 5K

When: Saturday, June 15, 9 a.m.

Where: Montauk Lighthouse, Montauk

Cost: $35 in advance, $40 day of.

What to Know: This 5K goes through Camp Hero and finishes at the iconic lighthouse — the perfect spot for a post-race snap. Proceeds to go Lucia’s Angels and the Coalition for Women’s Cancers.

The Shelter Island 10K is always a popular East End event. (Photo credit: Julie Lane)

Shelter Island Run

When: Saturday, June 15, 5:30 p.m. (10K), 5 p.m. (5K)

Where: 33 N. Ferry Road, Shelter Island

Cost: $45 (10K) and $35 (5K)

What to Know: The 45th annual run through Shelter Island’s low-key challenging hills brings locals to their lawns to cheer on runners (sometimes offering something other than water in hand).

Southampton Firecracker 8K/3-mile run/walk

When: Saturday, June 15, 5:30 p.m. (10K), 5 p.m. (5K)

Where: Agawam Park, 25 Pond Ln., Southampton

Cost: $39

What to Know: Firecracker runs are the Turkey Trots of July — if you know, you know. This event offers an 8K and a three-mile walk and run.

Lighthouse Triathlon  

When: Sunday, June 21, 6:50 a.m.

Where: Gin Beach, Montauk

Cost: $165 (by July 1), $170 after

What to Know: Start with a half-mile swim, bike 14 miles through gentle hills and finish with a 5K run that promises to be “scenic and satisfying.”

Jordan’s Run

When: Sunday, July 28, 7 a.m.

Where: 200 Jermain Ave., Sag Harbor

Cost: TBD

What to Know: This race is part of Suffolk County’s annual Veteran’s series. Proceeds from it go toward Jordan’s Honor, a non-profit established in the memory of fallen marine Jordan Haerter of Sag Harbor.

Southampton 5K Race of Hope

Audrey Gruss, Brooke Shields and Grier Hammond Henchy attend The 8th Annual Race Of Hope In Southampton at The Cultural Center on August 6, 2023 in Southampton, NY. (Photo by Sean Zanni/PMC/PMC)

When: Sunday, August 4, 8:30 a.m.

Where: Agawam Park, 25 Pond Ln., Southampton

Cost: $39 (by June 7), $35 (by June 12), $50 (by August 3), and $55 (race day)

(What to Know: A run through the scenic route at Agawam Park benefits Hope for Depression Research Foundation.

Ellen’s Run

When: Sunday, August 18, 9 a.m.

Where: 70 Leland Ln, Southampton

Cost: TBD

What to Know: This annual 5K helps people gain access to breast cancer health care through the Ellen Hermanson Foundation.

Hampton’s Marathon

When: Saturday, September 28, 7:30 a.m. (marathon/half marathon), 7:50 a.m. (5K)

Where: 70 Leland Lane, Southampton

Cost: $100 (Marathon before June 24), $110 (Marathon before July 29), $120 (Marathon before August 26) and $125 (Marathon, final), $85 (Half before July 29), $95 (Half before August 26), $110 (Half, final), $40 (5k before June 24), $40 (5K before July 29) and $45 (5K, final)

What to Know: The 45th annual run through Shelter Island’s low-key challenging hills brings locals to their lawns to cheer on runners (sometimes and offer of something other than water in hand).