There are times when you need to build in some mileage and you don't want to do anything complicated. Better yet, you might want to do some surges along parts of the route, or compare certain segment times with others. Or you're running with people who are doing a slower/faster pace than you, and want to all end at the same time. Or you want options to bail along the route. Regardless:
Below are three ideas, all starting and finishing at Prospect Park at the Grand Army Plaza entrance:
1) Crazy 8 Loops in Prospect Park: This one has the advantage of staying in the park and is a little less burdensome than trying to several 3.35 miles loops (though that's always an option). Start at Grand Army Plaza and take a left, going down the big hill. When you get to the first transverse (Center Drive), take a right. Follow the road until you reconnect with the big loop (West Drive). Take a left, and follow the roadway counterclockwise all the way back around to the Center Drive. Take a left, and repeat your trip up the transverse. This time, however, when you connect back with the West Drive, take a right and wend your way back to Grand Army Plaza. When you've completed the Crazy 8, that's 4.5 miles. For 18 miles, do four of them. (I'm reading this back and it sounds a lot more complicated than it is - basically whatever direction you go, run down Center Drive and choose the opposite direction).
ALTERNATIVE DIRECTION: When I've done this, I've alternated directions, partly for a change of scenery, partly because of the hills. Yes, you end up at the same place. But one direction has the big downhills, the other direction has the big uphills. The uphills (which you'll pick up if you start the route counterclockwise) are great for someone who wants to simulate some of the hills on Commonwealth Ave. in Boston during the Boston Marathon.
2) This one's just as simple, though, I'll leave it up to you what order you do them: Two loops of Prospect Park, and an out-and-back to Coney Island via Ocean Parkway. Prospect Park has hills, lots of water options (less so during the winter, but they are there in the bathrooms) and no/little traffic. Ocean Parkway has no hills, lots of traffic and virtually no water until you get to Coney Island, so either bring water or bring cash to buy water at one of the stores on the side streets. (RUNNING TIP: check out the hospital about 3/4 a mile from Coney Island). What I might do, especially if I'm running with people who may not want to do the full 18, is do a full loop of the park first, then head down to Ocean Parkway. The Ocean Parkway out and back is a bit more than 11 miles. You can also tack on some running on the boardwalk if you want to stay running on the flats.
3) Prospect Park, head over the Brooklyn Bridge, across Chambers Street to the West Side Highway for another 4.5 miles (up to about 64th St.) and then return. Did this today - couple of bathrooms at the 6/7 mile and 11/12 mile points make this a year-round option (and the bathrooms are relatively clean). The beauty of this route is that you can truncate the mileage at any point (run up to Canal Street and back for a 10 miler) or extend it past the GW Bridge.
There are plenty of other routes in Brooklyn that can get you the 18-20 miles distance, particularly if you run in Bay Ridge and head down toward the Verrazano Bridge, or if you head out near Floyd Bennett Field - yes, Brooklyn has a National Park, which is beautiful, though a bit isolated. The three I spelled out today have advantages is that they are all close to public transportation and give you bailout points, or opportunities to do more/less.
There are all fairly straightforward runs, so I'm not posting a map on this, though happy to do so if any of the above is confusing.
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