From the Berkshires and New York, take the Massachusetts Turnpike to Lee, Exit 2. Go left onto Route 20 (the Jacob’s Ladder Scenic Byway). A sign indicating the entrance to the Byway is located just before the Prime Outlets shopping center.
From northwestern Connecticut, take Route 7 north to Route 102 east in Stockbridge. Route 102 intersects with Route 20 (the Jacob’s Ladder Trail Scenic Byway) in Lee; go east on Route 20. A sign indicating the entrance to the Byway is located just before the Prime Outlets shopping center.
From the Boston or Springfield areas, take the Massachusetts Turnpike to Westfield, Exit 3. Go right onto Route 10/202 south, into Westfield Center. After about 2 1/5 miles (after crossing the Westfield River and immediately after passing under a railroad bridge), turn right on Route 20 west (Franklin Street). You will travel five (5) miles on Route 20 to the border with Russell, where a sign indicates that you are on the Jacob’s Ladder Scenic Byway (note the vast span of the Massachusetts Turnpike bridge passing overhead at this point).
Directions to the attractions (west to east)- Historic Downtown Lee
- First Congregational Church in Lee.
- Prime Outlets at Lee.
- October Mountain State Forest.
- The Appalachian Trail.
- Becket Arts Center of the Hilltowns.
- First Congregational Church of Becket
Turn north from Route 20 at Bonnie Rigg Corners onto Route 8. The church is on the left about 2 miles up the road, on the corner of Bennett Road.
Pine Hill Cemetery.About 1/2 mile west of the center of Chester, a narrow lane on the north side of the road climbs to the west past a small stone building (the cemetery vault). The cemetery is at the top of the lane.
Miniature Theatre of Chester.The Theatre is located at the Chester Town Hall, on Middlefield Street, just off of Route 20 (a left turn if you're coming from the west, left from the east). Parking is free in the school lot across the street. Handicap parking is on the street, in front of the town hall. There is a wheelchair ramp into the Theatre.
Chester Railroad Depot and Museum.Turn north onto Main Street Chester (left if you're coming from the west). At the end of the street, turn right and follow the signs.
Keystone Arch Bridges and Trail.It's advisable to call 413-354-7752 to arrange a guided tour and meet at the RR Museum (see above for directions). The arches are in a remote area that is accessible only by walking several miles. The walk is not difficult, but it isn't appropriate for the very young or the very old or people with mobility issues. As with any physical activity involving heights and unpredictable conditions, exercise appropriate caution. Please be respectful of the arches if you visit them.
Boston and Albany Railroad.The railroad parallels Route 20, beginning just east of the center of Chester and continuing to the eastern terminus of Jacob's Ladder Trail. The rails now belong to CSX and are heavily used for hauling freight. Amtrak's Lakeshore Limited also uses the tracks twice daily. There are numerous spots along Route 20 which afford good views of passing trains.
The Old Chester Jail.Immediately east of the intersection of Route 20 and Main Street, Chester, the jail sits on the north side of Route 20.
Westfield River.The West Branch of the Westfield River meets Route 20 at the center of Chester, visible on the north side of the road at the confluence with Walker Brook at Carm's. From that point to the eastern terminus of the Scenic Byway, the river parallels the road, always to the north. Just east of Huntington center, the West Branch joins the combined Middle, East and Dead Branches, creating the main stem of the river.
Chester Center on Skyline Trail.Coming from the west, travel about 3 miles east of Chester Factory Village and turn left onto Old State Road. After about 2 1/2 miles, turn left onto Cook's Hill Road. Follow that, bearing left at the next fork, about 5 miles to Chester Center. You'll see the Congregational Church and cemetery on either side of the road. From the East, turn right onto Rt. 112 in the center of Huntington, then make a hard left turn onto Basket St. immediately across the bridge. Follow that, bearing left at the first fork and staying along the river to a right turn onto Cook's Hill Road after about 2 miles. Follow that for about 5 miles to Chester Center.
Chester Hill Winery.From the west, follow Rt. 20 to Chester and turn left onto Middlefield Road (by the elementary school). Follow that about 2 miles, crossing over railroad and river bridges. Take first right, immediately after crossing the river, onto Johnson Hill Road. At that road's end, turn right onto Skyline Trail. Make your first left onto Lyon Hill Road. Take the next left (down the hill). The winery is on the right. From the east, follow Rt. 20 to Huntington and turn right onto Rt. 112, over the green bridge. Immediately across the bridge, make a hairpin left turn onto Basket St. At the fork, bear left onto Old Chester Road. At the next fork, bear right onto Cook's Hill Rd. (becomes Skyline Trail). At the next fork, stay left on Skyline Trail. Continue up hill, about 2 1/2 miles beyond Chester Center, to Lyon Hill Rd. Make a right onto Lyon Hill Rd. Take the next left (down the hill). The winery is on the right.
Chester-Blandford State Forest.Chester-Blandford State Forest abutts the south side of Rt. 20 for about 2 1/2 miles, from the Chester-Huntington town line on the east, to Sanderson Brook Rd. on the west.
H. Newman Marsh Memorial Trail.Park at the bottom of Sanderson Brook Rd. (about 3 miles east of Chester and 5 miles west of Huntington). Walk up Sanderson Brook Rd. (closed to vehicles) a short way beyond the first bridge and look for the trail head on the left of the road.
Boulder Park Accessible Trail.Boulder Park is adjacent to Rt. 20 about 1/2 mile west of the Chester-Huntington town line. It's distinguished by the row of larch trees separating the parking area from the highway. The ramp to the Accessible Trail is plainly visible from the entrance to the parking area.
Littleville Dam & Lake.In Huntington center, turn north on Rt. 112. Follow that about 1 1/2 miles to Littleville Rd.- a left turn immediately beyond the Huntington Country Store. Follow Littleville Rd. about a half mile to a right turn onto Goss Hill Rd. Cross the one-lane bridge and drive to the top of the steep hill. After about 3/4 of a mile, you'll see the access to the Littleville boat ramp and parking lot on the left.
Gardner State Park.In Huntington center, turn north on Rt. 112. Follow that about 3 1/2 miles. Gardner Park is on the left.
Huntington Country StoreIn Huntington center, turn north on Rt. 112. Follow that about 1 1/2 miles. The Huntington Country Store is on the left.
Knightville Dam & Wildlife Management Area.In Huntington center, turn north on Rt. 112. Follow that about 4 miles to a right turn onto Knightville Rd., a short way beyond the intersection with Rt. 66. At the end of the road, there's a picnic area and an access road to the dam. Continuing on Rt. 112 beyond Knightville Rd., there's an access road to the flood control basin on the right, just beyond Brookside Glen. Heed the signs regarding the flood conditions.
Countryside Woodcraft.About 2 miles west of the State Police barracks in Russell and 3 miles east of Huntington center, Countryside Woodcraft is on the opposite side of Rt. 20 from the river.
Hill & Dale Rapids.Immediately across the road from Countryside Woodcraft, a turnout provides parking for the Hill & Dale Rapids (named for a restaurant that formerly occupied the house adjacent to Countryside Woodcraft). The rapids are just upstream of the rest area (only during periods of high water).
General Knox Marker.There are two monuments to the passage of General Henry Knox and his troops, on their way to Boston during the Revolutionary War. One is located on Rt. 23 in Blandford and the other is on General Knox Road near South Quarter Road between Russell and Westfield.
Unfortunately, this site has been closed to the public since 2001.
Blandford Ski Area.From Mass Pike (I-90) exit 3: Turn right on Rte. 10-202 south to the center of Westfield. Turn right on Rte. 20 west. Go 8 miles to the Russell State Police barracks. (Do NOT turn up Rte 23 toward Blandford center) Turn left and follow the signs. Approx. 20 min. from exit 3. From the Berkshires: From Lee, take Rte. 20 east about 35 minutes to the Russell State Police barracks. Turn right and follow the signs.
Tekoa Mountain Wildlife Management Area and Rattlesnake Sanctuary.Mt. Tekoa is clearly visible from Rt. 20 on the north side of the river just upstream of the MassPike bridge at the eastern terminus of Jacob's Ladder Scenic Byway. There's no easy access to the mountain.
Leaving Jacob's Ladder Scenic Byway:
To northwestern Connecticut, about 1/2 mile south of the Lee town common and just northwest of the entrance to Prime Outlets at Lee, at the interchange for exit 2 off the Mass. Turnpike (I-90), turn west on Rt. 102. In the center of Stockbridge (after about 4 miles), follow Rt. 7 south to Litchfield County.
continue east on Rt. 20 about five miles beyond the Westfield/Russell town line (Mass. Turnpike bridge overhead) to the second traffic light ('T' intersection- you must turn either left or right). Turn left onto Rt. 10/202 (Elm St.). Proceed straight on Rt. 10/202 about 2 1/2 miles to the interchange with I-90 (exit 3 of the Mass. Turnpike). You must turn right (follow the signs) to enter the Turnpike (which is on the left). I-91 (points north or south) is four miles east at exit 4. Continue east on I-90 for Worcester, Boston and points east.
For the purposes of this website, Downtown Lee is the section of Main Street beginning at the common and ending at the bridge over the Housatonic River. Turn right at the bottom of the Exit 2 ramp from the Turnpike and proceed about 1/2 mile. The road turns left, then there is a hard right turn at the corner of the common. The Byway turns left at the north end of Main Street and brings you to the Housatonic River bridge in about 3/4 mile. Joe's Diner is at the left hand turn near the bridge.
You'll see this church at the north end of the common. Turn right at the bottom of the Exit 2 ramp from the Turnpike and proceed about 1/2 mile. The road turns left, then there is a hard right turn at the corner of the common. Look to your right as you are passing the common (there is parking in a number of places, including the east side of the common).
The Prime Outlet Center is just east of the interchange of Routes 20, 102 and Interstate 90 (Exit 2). Coming from the Turnpike, turn left onto Route 20 and proceed to the second set of lights. The Outlets are up the hill on the right.
From the Mass Pike (Rte. I-90 exit 2), turn right onto Route 20 west to Center St. in Lee, follow the state forest signs to the park.
The Appalachian Trail crosses the Jacob's Ladder Scenic Byway about 1/2 mile east of the Lee/Becket town line. Coming from the west, follow Route 20 about five miles and look for a rest area on the right side of the road. From the east, look for the trail crossing about 1/2 mile after you've passed Greenwater Pond. Park in the rest area and check the informational kiosk for more information.
From the Mass. Turnpike Exit 2, turn left onto Route 20 East. Approximately 8 2/10 miles east on Route 20, make a left on George Carter Road. Travel 6/10 of a mile and make a right into the entrance of Jacob's Pillow. Traveling from the east, George Carter Road will be on the right, about 2 1/4 miles past the Cairn.
From the west, travel about 10 miles east on Route 20. Look for the deer statue on the left at the crest of the hill past Becket Woods. The cairn is immediately beyond the adjacent building (the former Summit House). From the east, the cairn is about 3 miles beyond the intersection with Route 8 north at Bonnie Rigg Corners on the right.
From the west, follow Route 20 east about 13 miles to Route 8 north (the second intersection with Route 8). Follow Route 8 north about 9 miles. The Arts Center is on the left at the corner of Hill Rd. Route 8 north is about 5 miles west of Chester center.
Coming from Lee, you will pass by Fred Snow at the cairn. Continue on Route 20 to Route 8 north, then continue about 6 miles north before you turn left onto Fred Snow Rd.