Available distances
About
Cupid's Chase 5K Annapolis is held in Annapolis, Maryland, on February 13, 2027, with a single 5K (3.1 miles) starting at 10:00 a.m. Elevation gain is not listed for the course. The mid-morning start is a friendly one for a February race, since it gives the air a few hours to warm before you line up.
Valentine's weekend 5Ks tend to draw a mixed field, which makes them a comfortable place to run your first race and still a legitimate test if you want to push. To race it, spend the last three weeks doing one interval session and one steady 20-minute run each week, and keep everything else easy. To simply finish it, three run-walk sessions a week for a month is plenty. Either way, arrive early enough for 10 minutes of jogging, because a cold start line and a fast opening quarter mile are a bad combination.
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An AI-generated training plan, adjusted every week based on your real sessions. Built around your goal, current level and race date.
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Races nearby
Other upcoming races around Annapolis.
Bay Bridge Run
Nov 8, 2026 · Annapolis, MD · 4 mi away
6.2 mi
Stocking Suffer 8-Hour Endurance Run
Dec 6, 2026 · Stevensville, MD · 9 mi away
8 h
Downs Park 5 Miler
Nov 7, 2026 · Glen Burnie, MD · 11 mi away
5 mi
North Linthicum Improvement Association Turkey Trot 5k and Fun Walk
Nov 14, 2026 · Glen Burnie, MD · 18 mi away
3.1 mi
LARS Race Against Hunger & Homelessness
Nov 26, 2026 · Laurel, MD · 21 mi away
3.1 mi
Angels on the Run - Elkridge
Nov 14, 2026 · Columbia, MD · 21 mi away
3.1 mi