Written Directions
This route starts and ends at the Queens Midtown Tunnel in Manhattan.
Head north on FDR drive, continue north on Buckner expressway, continue north on Hutchinson River pkwy, continue north on I-684 and exit on S. Bedford Road (Route 172) and head northeast up to Route 35. Take Route 35 east to Route 102 east. When 102 runs into Highway 7, go right (south) for just a short 2000 feet, and get on to Route 107 and take it north and vere to the left on to Umpawaug Rd until it runs into Route 53. Here take a right (head south) and head past the Saugatuck Reservoir till 53 meets up with Route 57 where you want to take a left and head south down to Route 15. At route 15 take a right and head southwest down to Rye Brook where you will complete a loop when you meet up again with Hutchinson Pkwy and take that south and your original roads to end up where you started.
Scenery
This is great Sunday afternoon - very green/rural with 5-star food/drink stops! Very green and rural, beautiful twists and lots of water (ponds, reservoirs, etc), really feel like you got out of the city. Affluent area with lots of huge houses and horse farms.
Drive Enjoyment
Perfectly paved rural roads, also the wonderful green racetrack that is the Merritt Parkway.
Tourism Opportunities
Great run from Manhattan for the afternoon. Beautiful pastoral scenery near Bedford, have champagne brunch at the Bedford Post Inn (stop 1 on map) on the terrace (a Relais & Chateau property) https://bedfordpostinn.com/barn and/or down the road at Le Chateau https://www.lechateauny.com/ (stop 2 on map), a beautiful French restaurant in a converted mansion with Hudson Valley views and a white-glove brunch service. Take a run on Umpawaug Road, a CT Scenic Road, before you drop by for a beer at biker-friendly Squire's Redding Roadhouse (stop 3 on map), a tavern in the woods with an outdoor patio, that used to be a biker bar. Head down to the fantastic Merritt Parkway (green, twisty, fast) to take it on home back to NYC.