Maryland in late fall is a gift to runners. The summer humidity has finally let go, the leaves are down or on their way, and race morning air has that crisp edge that makes 13.1 miles feel a whole lot more doable. Whether this is your first half or one of many, November and December are prime time to chase a finish line here — and there are five upcoming half marathons in Maryland in this window, with four worth circling right now.
Here's a look at each, in order of race day, so you can plan your season before the good ones fill up.
Schaeffer Half Marathon, 10K, 5K Trail Run — Saturday, November 7, 2026
Germantown
If you've been curious about trading pavement for dirt, this is a gentle way in. The Schaeffer Half in Germantown is a trail run, which means softer footing, a little more attention to where you're stepping, and a morning that feels more like an adventure than a time trial. Early November is a sweet spot for trails — cool enough to work, not so cold that you're second-guessing every layer. A solid pick for runners who want something a little different from their usual road half.
Freedom is Never Free 5K, 10K, & Half — Sunday, November 8, 2026
Potomac
The very next day, over in Potomac, this race offers a half alongside shorter 5K and 10K options — handy if you're bringing a friend or family member who isn't quite ready for 13.1 yet. A Sunday race means a Saturday to rest, pick up your packet, and lay out your gear without rushing. It's a welcoming, community-minded kind of morning, and a good fit if you like your fall races with a little meaning behind them.
NCR Marathon & Half Marathon — Saturday, November 28, 2026
Sparks Glencoe
Thanksgiving weekend, and a race that gives you a reason to earn the leftovers. The NCR Half in Sparks Glencoe lands on Saturday, November 28, which makes it a nice bookend to the holiday — run first, feast later. Late November mornings can be chilly, so plan your layers, but the payoff is a quieter, focused kind of race day. With a quality score of 73 out of 100, it's a standout choice for runners who want a well-regarded half without the big-city circus.
Naptown Half Marathon & 10K/5K — Saturday, December 19, 2026
Annapolis
Closing out the season in Annapolis, the Naptown Half is the highest-rated of this bunch at 74 out of 100 — a runner favorite in our book. A December race in a waterfront town has a certain charm: crisp air, holiday lights starting to show, and a finish line that feels like a proper end-of-year reward. If you've been chasing a goal all fall, this is a lovely place to cash it in. The accompanying 10K and 5K make it easy to turn race day into a family outing.
Which one fits you?
First-timer? The Naptown Half's December date gives you the most training runway, and Annapolis is a forgiving, friendly place to debut. Chasing a fall goal before the calendar flips? NCR on Thanksgiving weekend is a strong pick. Want something off-road and a little wild? Schaeffer's trail half is your adventure. And if you're rounding up the crew, the Freedom is Never Free race has distances for everyone.
Whichever you choose, register soon — late-fall races have a way of sneaking up, and the good ones don't stay open forever.
Ready to see the full slate? Head to our half marathons in Maryland directory for every upcoming race in the state, and start planning your next 13.1.