Here are some of my favorite routes, which I usually rotate through at least once in an average week (in New York, anyway).For descriptive purposes, some loops are assigned the name of the location I typically wind up at the halfway point.
NEW YORK CITY
Central Park (11.3M) (map)
This is my typical Monday running route; I love starting the week by facing down the hills in this beautiful park. I almost always run counterclockwise, which I think is actually a bit frowned upon. I try to make up for this weekly breach by being unnervingly friendly to all of the runners passing in the other direction.
Hudson River Park Greenway (11M) (map)
A favorite especially in springtime, when all the cherry blossoms are in full bloom, this route is also really wonderful for sunrises and sunsets: Sunlight dances across the river, and New Jersey never looked so lovely.
Morningside Heights (11.1M) (map)
The heights that Morningside is named for can certainly be a bit brutal, but hill work is good for you, right? Also, Riverside Drive is one of my favorite streets to run along home: It's quiet, tree-lined, and full of good peeping-into-wealthy-people's-apartments opportunities.
Tompkins Square Park (10.5M) (map)
Yes, I really do run around Tompkins Square Park three times during this jog. Yes, Tompkins Square Park is a little bit crusty. Yes, this entire route smells pretty funky come August. But somehow, it remains one of my weekly favorite trips around the city. I guess it just feels authentic somehow? (Bonus: Sometimes, on less-humid days, Chinatown smells more like star anise and fresh-baked buns, less like the previous day's rotting cabbage.)
Sutton Place (10.2M) (map)
Technically, this isn't a great name for this route: The halfway point is closer to the eastern edge of Central Park. But somehow Sutton Place is what stands out for me here—the rest is cake.
Lake Hefner Trails (10.8M) (map)
Whenever we're in Oklahoma City visiting my in-laws (the winter holidays, for instance, and sometimes the days before and after traveling to the Red River Rivalry in Dallas), I make a point to run around this beautiful lake. It's got everything: Gently rippled water, cranes, beautiful sunrises, flat straightaways, smooth pavement, limited one-way traffic, parking (!)… and a whole lot of totally unforgiving wind. Oh well. Can't have everything!
09/30/12 Maine Marathon; Portland to Yarmouth, ME
10/14/12 Grete's Great Gallop (13.1M); Central Park, NY
10/28/12 Poland Spring Marathon Kickoff (5M); Central Park, NY
11/18/12 Race to Deliver (4M); Central Park, NY
Races I've run
04/23/11 Run As One NYRR (4M): 30:06
06/25/11 Front Runners NY Gay and Lesbian Pride Run (5M): 40:58
07/16/11 Central Park Conservancy's Run for Central Park (4M): 31:30
09/17/11 Women Mind Body Spirit Games (4M): 29:42
11/20/11 The Race to Deliver (4M): 30:51
02/05/12 NYRR Gridiron Classic (4M): 34:59
04/15/12 MORE + Fitness Magazine Half Marathon: 1:59:35
05/12/12 UAE Healthy Kidney 10K: 50:32
05/19/12 Brooklyn Half Marathon: 1:47:40
06/23/12 Front Runners NY Gay and Lesbian Pride Run (5M): 42:03
07/14/12 Run for Central Park (4M): 31:28
Resources for finding races and route information
MapMyRun.com Check out other users' favorite routes using this GPS-based tracking gizmo. Download the iPhone or Android app to join the fun (though I've found the satellite tracking to be unreliable), and share your own well-worn paths with other runners.
Marathon Guide Plan a destination marathon, or organize your next vacation around a new running location with this handy search tool. (It includes reviews of races from past participants, and links to registration as well as contact information for race organizers.)
Runner's World Race Finder Not the most complete race-search engine on the Internet, but a great start, especially if you want to stay relatively local to your home base.