30 to 60 miles depending on the route
This Legendary Ride is said to have originated in the 1940’s. The ride take it's name from the defunct Gimbels Department Store, now Stern's, at the Cross County Shopping Center where it departs at 9:15 sharp. With its reputations for attracting some of the best riders on the east coast many first timers are more nervous about the prospect of getting deposited in the foreign soil of Westchester, a particularly unnerving scenario for hardcore NYC residents….
It is especially fast in the spring when local strong men and the occasional pro are known to terrorize the peleton. At about 9:40 the ride passes route 119 on to route 22 to the Kensico Dam where the pace picks up. At this point riders have a choice between the short option, which continues North On Rt 22 to Rt 433, or the long.
The long ride bears left onto Rt 120. This hilly section intersects Rt 117, where the riders turn right in Chappaqua (at the bottom of the steep hill). Another few miles of undulating roads the riders turn right onto Route 128. After negotiating a single hill the course proceeds left on Rt-22 (via the town of Armonk). Make a right onto Rt 433 (Riversville Rd) and the next right onto Bedford Road. This circuitous section takes the riders up a short steep hill (Picket Fence Hill) and right onto Locust road. Riders follow the road around a very sharp left turn only to make next right/left combo onto Rt-120 (Concrete Road 'white' adjacent to West.Cnty Airport). Flat road continues until left turn on Purchase Street. Up a gradient (referred to as 'the suppressor'). This mainly 'fast' section proceeds approx. 4.0 miles to the 'midway sprint' of the ride (green sign just prior to sharp right over I-287 Overpass). Make left and head down hill (adjacent to highway). Bear right at bottom of hill onto Purchase Street (Up a hill). Continue through intersection onto flat area (known as the 'Tibetan plateau'). Road descends while making sweeping left and sweeping right. Sweeping right flows riders naturally onto Wappanocca Ave (concrete road). At intersection make left on Cedar St and right back onto Purchase Street (under I-95 overpass). Make immediate right onto Theodore Friend Ave (undulating) and left onto Hammond Rd (short distance). Bear left onto North Street and up the last hill of the ride (referred to as the 'Poggio'). Road merges onto Boston Post Rd (Rt 1). Take approx. 3mi to finish (bottom of gradual hill, green sign just prior to Harrison Ave. mark the line). Both the long and short versions of the ride end on Boston Post Rd. in Mamaroneck.
Some say the only thing as difficult as riding the Gimbels is getting there. Riding, driving, and public transit directions to the Gimbels Ride thanks to Kissena team member James Leiken:
Easy way: ride to Grand Central, take Metro North (8:23am train recommended) to Hartsdale Station, take Hartsdale Ave. (right turn out of depot) to Central Ave., turn left (south), and ride slow until you see the group coming the other way.
Less Easy way: Follow directions to GWB and continue straight under bridge. Right turn on 181st, left on Broadway. Follow Broadway into the Bronx (suggest using sidewalk over Broadway Bridge–steel grid deck), and turn right on 238th St., cross over Deegan Expwy. Bear straight uphill (Orloff Ave.?), bear left across Van Cortlandt Ave., next right onto Van Cortlandt Park So./Gun Hill Rd. Turn left on Jerome Ave., under elevated subway. Turn right on E. 233rd St., next left on Van Cortlandt Park East. Becomes Kimball Ave. Continue to Cross County Shopping Center (entrance is on your left, just before the Cross County Parkway. Ride starts near Stern's dept. store, about 9:15am, Saturdays and Sundays. Approximately 25mi from Brooklyn Bridge.
You can shorten the ride by taking the 4 train to the end (Woodlawn), and pick up the route on Jerome Ave. You can also try taking the 2 train to the end (Wakefield/241st), and ride west on 241st/Wakefield Ave. to Kimball Ave., although I've never done this. I suggest bringing along Hagstrom's Lower Westchester County map.
The original 'G'–Local legend Bill Montgomery. Some swear he was on the first Gimbels ride ever, and in those days you had to contend with the hills and the Indians...
Before you depart sample some of the local cuisine, you will need it.
Like we said be careful, guys are out for blood on this thing.