37th Anniversary Hemingway 5K Sunset Run & Paddleboard Race

Hemingway 5K Sunset Run & Paddleboard Race at Southernmost Beach Café

Hemingway 5K Sunset Run & Paddleboard Race 2026 — Key West’s Iconic Summer Challenge

Date: Saturday, July 25 – Sunday, July 26, 2026
Location: Southernmost Point & Southernmost Beach Café, Key West, Florida

The Hemingway 5K Sunset Run & Paddleboard Race returns to Key West in 2026 as one of the most anticipated highlights of Hemingway Days. This two-day event combines endurance, island fun, and the festive spirit of summer in paradise. Athletes, walkers, and festival-goers gather at the Southernmost Point and Southernmost Beach Café to compete, celebrate, and honor Ernest Hemingway’s adventurous legacy.

Event Highlights

• 5K Sunset Run & Walk
  Starting at 7:30 PM on Saturday, July 25, the race begins at the iconic Southernmost Point Buoy. Participants follow a scenic route through Old Town at golden hour, with divisions for both competitive runners and casual walkers.

• Beach n Beer Mile
  At 12:00 PM on Saturday, July 25, the Southernmost Beach Café hosts a spirited one-mile dash across the sand, where every lap is paired with refreshing brews.

• Virtual 5K Anywhere
  Those unable to attend can still join the tradition by completing the 5K virtually, running or walking from any location around the world.

• Awards Ceremony & Beach Party
  The celebration begins at 8:00 PM on Saturday with live music, tropical cocktails, and island nightlife vibes at Southernmost Beach Café.

• Paddleboard Race & Wrap-Up
  On Sunday, July 26, paddleboard competitors take to the turquoise waters for an exhilarating finish to the weekend’s activities.

Why Join the Hemingway 5K Sunset Run?

• Scenic Island Setting — Race along the southernmost streets in the continental U.S., just steps from the ocean.

• Festival Energy — A core event of Hemingway Days, blending literature, sport, and island celebration.

• Diverse Challenges — From a competitive 5K to a casual walk, paddleboarding, or the lighthearted Beer Mile, there’s something for every type of participant.

• Unforgettable After-Party — Celebrate with music, food, and drinks under the stars at Southernmost Beach Café.

2026 Schedule at a Glance

Saturday, July 25, 2026

• 12:00 PM — Beach n Beer Mile @ Southernmost Beach Café

• 7:30 PM — 5K Run & Walk Start @ Southernmost Point

• 8:00 PM — Awards & Beach Party @ Southernmost Beach Café

Sunday, July 26, 2026

• Paddleboard racing & Hemingway Days closing activities

Registration is open now for the Hemingway 5K Sunset Run & Paddleboard Race 2026. Whether running for a personal best, walking with friends, or joining the after-party, this event is where sport meets celebration in the heart of Key West.