Near Washington and New Milford, the 750 acre Steep Rock Reservation contains a network of 15 miles of roads and trails climbing out of the Shepaug River valley. All trails are open to hiking. Horseback riding and mountain biking are permitted on posted trails and carriage roads only.
To reach Steep Rock, follow Saw Mill River Parkway north to US 684 north to US 84 west; exit 7 for Route 7 north (set the odometer at 0); at 11.8 miles turn right onto US 202/Bridge Street in New Milford; at 20.0 miles turn left onto Route 45 north; at 20.6 pass West Shore Road and Lake Waramaug; turn right onto Route 47 south; drive 1.9 miles to the Bee Brook Parking Area on the left; park on either side of the bridge over the Shepaug River.
From the parking area north of the Bridge over the Shepaug River there is a short circular walk on the white-blazed Bee Brook Trail (sandwiched between Bee Brook on the west and the Shepaug River on the east and south). This trail can be expanded by hooking up with trails on the other side of the Shepaug River. There is a bridge over the river on the east side of the Bee Brook Trail that joins with the yellow-blazed Van Sinderen Trail).
From the parking area south of the Bridge over the Shepaug River, you can choose one of three different tiers of trails. (At times you can see people walking on all three levels at the same time.) There is an unblazed trail that parallels the southern shore of the river (and crosses over the river to the white trail). There is a second tier trail (yellow-blazed) that also parallels the river at first but then heads eventually to the pinnacle and later north to the look-out point. And there is a third tier that eventually goes to the blue-blazed Pinnacle Trail that from the pinnacle heads southeast and then northeast to the East Entrance on Sabbaday Lane.
The Van Sinderen Trail from the south eventually hooks up with the red trail that becomes a three and one half mile loop trail (if you wish to take the circular part of the trail). It is all a little confusing so, study the trail map at the kiosks. You may want to draw it out on paper and carry along a compass (which you should always have with you anyway when you are hiking). There is an old quartz mine on the Van Sinderen Trail. The mine was active from the mid 1800s until 1915. The quartz was transported by wagon to the Hudson River, at first by wagon, and later by rail. (There is still indications of the old railroad spur and a cut for hand carts.)
Overall, Steep Rock Reservation is the 12th most popular hiking trail of all 16 hikes in Connecticut.