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Scenic Drives
Litchfield/Northwest
Litchfield/Northwest Region Drive 1
Begin at the New Milford Green, and take CT Route 202 West to Route 7 North. Take Route 7 through the towns of New Milford, Gaylordsville and Kent. Outside of Kent, pick up Route 45 South to Warren. Drive around Lake Waramaug into New Preston. In New Preston, take Route 202 East to Route 47 South. Take a right onto Route 199, and then right on Route 67. Follow Route 67 to the junction of Route 202 in New Milford where the drive began. This drive is 64 miles and takes about 1/2 day. The route will take travellers past the Housatonic River, Bull's Bridge (one of only two covered bridges in Connecticut), the town of Kent and its many art galleries, historic homes and churches in Kent and Warren, Lake Waramaug, Mt. Tom State Park, the historic Mine Hill Preserve (ruins of an early iron mine), and the Institute for American Indian Studies. 
Litchfield/Northwest Region Drive 2
Begin in Torrington at the junction of Route 8 and Route 4. Take Route 8 north into Winsted, where it will intersect Route 44. Take Route 44 east into New Hartford. In Hartford pick up Route 219 north through Lake McDonough to Route 318. Continue on Route 318 west and 181 south for 1 mile, then make a right just before the metal bridge and take the road through the People's State Forest to Route 20 in Riverton. Take Route 20 west through Riverton and at the junction of Route 8, take 8 south into the center of Winsted. Pick up Route 44 west and take it to Route 183 north into the center of Colebrook. From Colebrook take Route 182A to 182, and make a right on 182. At the intersection of Route 44, take 44 west into Norfolk. In Norfolk, pick up Route 272 South into Torrington. Take 272 to Route 4 east, bear right onto Main Street. Where Main Street meets Route 202, take 202 east to the junction of Route 8 and 4, where the trip began. This tour is approximately 68 miles. 
Waterbury
From I-84 in Waterbury, begin at Route 8 north to Exit 38. At the end of the exit ramp, make a left. Travel down to the first traffic light and make another left. You should now be on Route 6. At the next stop sign go left again. Make sure you stay on Route 6 through the traffic light, and continue on until you spot the entrance to Black Rock State Park, make a right and enter the park. Enjoy the park scenery, and upon exiting the park, take a right back onto Route 6. Follow the road into Watertown, and at the intersection of State Route 63, make a left. Follow Route 63 into Middlebury and to the intersection at Route 64. Make a right onto Route 64 and follow it down about 4 miles to Route 188, where you'll make a left. As you continue on Route 188, you'll pass Rose Hurst Stables on the left. Continue on Rte 188 for 5 miles to Route 67. Turn left onto Route 67 South. This will take you through Oxford and then into Seymour. In Seymour, pick up Route 8 North and take it back to Waterbury.The time of the drive, without any stops, is approximately 1 hour and 15 minutes. 
Mystic/Eastern
River Road - Pequot Trail – Route 1
Start in Downtown Mystic on the Groton side of the drawbridge by turning onto Pearl Street. After a few blocks of charming homes you will see the Mystic River on the right. Stay close to the river and you will be brought onto River Road, which meanders alongside the river to Old Mystic. River Road is used by many walkers, runners and bikers so please drive slowly and enjoy the views. Shortly after you pass a cemetery on the right you will come to a traffic light. You are now in Old Mystic. Turn right at the light and then turn right at the stop sign on to Route 27 South. Just past the view of the river on the right, and the refurbished brick mill, turn left onto Route 234-Pequot Trail. The road climbs quickly and sharply and then gently twists and turns through Stonington. Follow the route 234 signs. When you reach the traffic light at Route 1 turn sharply to right onto Route 1 South. Follow Route 1 back to Mystic. Total drive time is about one-half an hour. 
Routes 49 and 14A
A State Scenic Highway, Route 49 begins in North Stonington, in Southeastern CT, and runs north to Route 14A in Sterling. Along the way, travelers enjoy dramatic vistas viewed from large hilltop farms. Three of those farms have been used by the same families continuously for almost 300 years. This route runs for 19.5 miles north to the Sterling Hill National Register Historic district. Offering views of fields and farms, it's a great way for visitors to nearby Mystic (in Southeastern CT) to extend their trip northward to Northeastern CT.
North Stonington - Plainfield
Route 169
The Norwich-Woodstock Turnpike, Route 169, runs for 32 miles from Canterbury to Woodstock. It's the longest scenic state highway in Connecticut, and offers views of historic sites, rolling hills, gentle woodlands. An estimated 189 pre-1855 homes survive along the highway, as well as historic churches and farms. The highway winds through the towns of Lisbon, Canterbury (home to a confluence of Georgian architecture), Brooklyn (the "other" Brooklyn), Pomfret (once known as the "other Newport" for its strong influx of wealthy vacationers), and Woodstock, which has an architectural feast surrounding a traditional New England town green.
Canterbury - Woodstock
Connecticut River Drive
Route 82 offers some spectacular views of the Connecticut River Valley countryside. Begin at Exit 7 off Route 9 in Chester and wend your way through a portion of the Cockaponset State Forest. The road then crosses the Connecticut River into East Haddam, offering a stunning view of both the Goodspeed Opera House and Gillette Castle. You'll meander through the village of East Haddam, past the opera house, and then back into the countryside. The road also goes right through Devil's Hopyard State Park, before continuing east into Salem and Norwich in the eastern part of the state. 
Shoreline Town Drive
For a scenic trip through the shoreline towns of Old Saybrook, Westbrook, Clinton, Madison, Guilford and Branford, begin in Essex and take Route 154 south into Old Saybrook. 154 goes right through the center of Old Saybrook and then heads out to Saybrook Point where it turns and follows the coastline. Great waterviews can be found all along the route, but the scene of the Sound from Saybrook Point with the homes out in Old Lyme in the distance (assuming good visibility) is unforgettable. In Westbrook, 154 will intersect with historic U.S. Route 1. Following U.S. 1 west into Branford (where you can pick up I-95 for a speedier trip from there) will take you through traditional New England village centers, past numerous shoreline and marina settings, and even near to the popular Hammonasset State Beach. 
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