Winter Wonderland 5 Miler 2027 — Milford, CT
Winter Wonderland 5 Miler costs $20 to $30 to enter. The race takes place in Milford, Connecticut on January 31, 2027, with a 9:30 AM start time. The event features a single 5-mile running distance, making it accessible for runners training at various levels. Early registration is recommended given the straightforward pricing structure and established start window. Milford's location in coastal Connecticut provides a convenient option for regional runners looking to maintain fitness during winter months.
Course & Travel Notes
Plan for cold conditions in late January at Milford, Connecticut, with typical highs around 38°F and lows near 24°F, so bring warm layers and consider rain gear since about a third of days see measurable precipitation. The race takes place at a very low elevation of just 39 feet, so elevation won't be a concern. With sunrise at 7:04 AM and the 9:30 AM start time, you'll have good morning daylight. Igor I Sikorsky Memorial Airport is conveniently located just 5.4 miles from the venue, making it an easy drive to the race.
Hotels Near This Race
Find accommodation close to the start line in Milford, CT. Sorted by distance from the race venue. Book early — race weekend hotels fill fast.
Winter Wonderland 5 Miler 2027 — Milford, CT
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Race Travel Insurance
Don't forget travel insurance for January 31.
You've trained for months and booked a trip to Milford, CT. A pre-race injury, a delayed flight, or a family emergency can derail the whole thing. Travel insurance can help cover your race entry fee, hotel, and flights if you can't make it, and may cover medical costs if something goes wrong on the course. Plans typically only run 5-7% of your total trip cost — and running events are covered under standard plans with no additional coverage needed.
- Trip cancellation up to 100% of prepaid costs
- Running events covered under standard plans — no add-ons needed
- Trip interruption up to 150% of non-refundable costs
- Emergency medical up to $250,000
- Cancel For Any Reason add-on available
- 24/7 real-time support
Affiliate links — we may earn a commission at no cost to you. Coverage terms vary by state and plan. Review policy details before purchase.
Frequently Asked Questions
When is Winter Wonderland 5 Miler 2027 — Milford, CT?
Winter Wonderland 5 Miler 2027 — Milford, CT takes place on January 31, 2027. The race is held in Milford, Connecticut.
Where is Winter Wonderland 5 Miler 2027 — Milford, CT held?
Winter Wonderland 5 Miler 2027 — Milford, CT is held at P.O. Box 57 in Milford, Connecticut.
Where can I find hotels near Winter Wonderland 5 Miler 2027 — Milford, CT?
RaceHotelFinder shows hotels sorted by distance from the race venue in Milford. Use the map or list view on this page to compare options and book race weekend accommodation.