Peabody, MA | NOVEMBER 9, 2025
Fast Times. Big Prizes.
A unique race in New England: We're giving away 17 FREE trips for a race weekend in Bermuda and you can win in one of two ways: Run one of the top times in the 1 mile race on the track OR register for either the mile or the 5k and be entered into the raffle. Free trips include airfare, hotel, and registration for the Bermuda Triangle Challenge January 15-18, 2026! We are incredibly grateful to BTC for working with us again this year!
New for this edition: We have added a 5k on Bishop Fenwick's beautiful cross-country course. Participants in either the 5k OR the mile are eligible to win the free trips via raffle.
Here's some even better news: If you're not lucky enough to win a trip, you can still go to Bermuda! Check out the Bermuda Triangle Challenge website to learn more about this fantastic race weekend and how to plan your trip.
Event Address: Bishop Fenwick, 99 Margin St., Peabody, MA 1:00pm
About the Race
We developed an exclusive partnership with a race weekend in Paradise: Chubb Bermuda Triangle Challenge. The weekend has three race days, starting with a nighttime road mile under the lights called The Butterfield Mile. The entire city comes out to watch this electric event. We are honored to hold a qualifying event here in New England for the Butterfield Mile. Each year, we hold our race in November, and we send a lucky group of runners to Bermuda for free, to participate in the Butterfield Mile along with the rest of the Bermuda Triangle Challenge. You can win a trip by dropping a fast time OR by having your name pulled by random lottery. The prize breakdown is as follows:
- Top 4 Open Men
- Top 4 Open Women
- Top 2 Masters Men
- Top 2 Masters Women
- 4 Raffle Winners
The fine print:
- The mile race will be broken into heats. Generally, they will be divided into heats based on age, then seed time. If a Masters runner drops a faster time than an Open runner, the Masters runner will take the Open Prize slot.
- No double dipping. If an athlete wins a prize based on time, they will not be eligible for the lottery.
- The raffle is open to all registered athletes.
- Prizes include:
- Free Race Entry to the Butterfield Mile and any other race under the Chubb Bermuda Triangle Challenge. The event is Friday, January 16 to Sunday, January 18, 2026.
- Flights: Offer up to $600 per person. Athletes are not entitled to any balance for flights that are less than $600. (Race Director's Note: In our experience, this has always covered the full cost of the flight).
- Hotel: Grotto Bay Beach Resort and Spa, Bermuda. Accommodation based on double occupancy.
- Length of stay: 4 nights only.
- All Athletes are to arrive on Thursday (January 15) before the Chubb Bermuda Triangle Challenge event and leave on Monday (January 19) after the Chubb Bermuda Triangle Challenge Butterfield Mile event.
- For athletes wishing to stay longer, accommodation and other extra fees will be incurred by the athlete. There are discount rates at Grotto Bay Beach Resort and Spa Bermuda and other hotels. Please refer to the website: Chubb Bermuda Triangle Challenge | Hotels.
- The stay does not cover food and drink costs. That is borne by the athlete.
- Other benefits: athletes are entitled to free shuttle pass(es) to the Butterfield Mile.
If you'd like to get in touch with us, please contact us at director@themayorsmile.com
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