Western Massachusetts  |  Western Connecticut

Taking a scenic drive through "The Berkshires" is time honored tradition. It goes all the way back to when the first car cruised through. My grandmother used to tell me how they would just find an open field, pull over, and have a picnic. "This land is your land, this land is my land...". These days, you'd probably get yelled at or arrested for doing something like that :) - but there are still plenty of great spots to check out and enjoy and put down a nice picnic if you so choose. Nearly everyone gets an itch to drive "up the line", out into the mountains, or through farmland. Western Massachusetts and Connecticut, along with the Hudson Valley of New York, offer some of the most picturesque drives in the world - no exaggeration. There may be mightier places with chiseled mountainsides and grander expanses of land but no where will you find the diversity of terrain and history as in this region. Colonial New England with its white clapboard churches, dirt roads, and covered bridges is as easy to find as the modern mall or suburban sprawl. The Housatonic River, Connecticut River, Hudson River are the major waterways running north/south and help shape mountains and hills named Berkshire, Litchfield Hills, Shawangunk, Catskill, Adirondack.



A little farther north of the Berkshire Mountains are the larger Green Mountains of Vermont and White Mountains of New Hampshire. Though our highest peaks aren't as high as those in the West, we are more or less just off the shores of the Atlantic Ocean (there's not a spot in New England that isn't more than a few hours from the ocean) whereas our Western counterparts enjoy mile high flat lands. Their magnificent peaks reach 10,000 feet and beyond...but they've got a 5,000-8,000 foot head start since their mountain bases are a mile high or more! It's all relative. I've met a couple from the Swiss Alps who prefer the Taconic Plateau to their mighty mountains. Indeed, the mountains of the Northeast are impressive just like any other mountains and the views spectacular since they rise up thousands like any good mountain should. Because of nature's long erosion process, they're softer and rounded over, and therefore more inviting. There is just something sweet about a winding, southern New England valley bolstered by hills and mountains on either side with countless trees. Hop in a car, on a motorcycle, on a bike, or take a scenic flight, and head north away from New York City. It won't take you long to get away from it all.

Western Massachusetts

1)  Route 7
Running north/south in the extreme western part of the state, Route 7 will take you through the heart and soul of The Berkshires. Berkshire County boast all sorts of natural wonders and historical gems. The towns/cities of Ashley Falls (Bartholomew's Cobble is a neat place), Sheffield, Great Barrington, Pittsfield, Lanesborough (home to Berkshire Mountains' highest peak, Mount Greylock - 3,941 feet), and North Adams; just some of the spots on or nearby Route 7. It's classic colonial New England mix right in with the modern world. Visit Monument Mountain where Herman Melville and his buddies, Nathaniel Hawthorne and Oliver Wendall Holmes, helped him form one of the great sea adventures, "Moby Dick". This is a can't miss drive no matter where you go. Lots of places to stop for nature or to shop and eat if that's your thing. If you're planning a road trip to eastern Canada, Route 7 gets even better through Vermont and Lake Champlain then eventually crosses over into Canada and becomes 133 and continues on to Montreal. If you have the time, consider driving it.
Google Map search, "Pittsfield, Massachusetts" then zoom in and out for maps and create custom driving directions to print out and take with you.

2)  Route 2
Running west/east the length of Massachusetts not far from the Vermont and New Hampshire border, Route 2 will also take you through the heart and soul of The Berkshires just as Route 7 does in a north/south direction. Located in the northwestern part of the state, this portion of Route 2 would have to be listed as a top 10 stretch of road for all of southern New England. Williamstown, about a half hour southwest of New York's capital of Albany, is nestled into a spot near where Massachusetts, New York, and Vermont meet. The town is home to Williams College and is loaded with historical significance and magnificent scenery. Just west of Williamstown is the great town of North Adams, which lies just north of Mount Greylock. North Adams is a perfect blend of small town life with a big city attitude. There's a thriving art community with world class museums and any type of food imaginable. Continuing farther west is Greenfield and Deerfield...both very interesting spots with Deerfield home to a small historical town where folks reenact colonial times. If you live in Boston, Route 2 would be one nice ride once you got beyond surrounding suburban sprawl. New Yorkers would likely need to make a weekend out of it or at least an overnighter but cruising up Route 22 back and forth in one day is doable if you love to go for LONG drives - 3 hours one way.
Google Map search, "North Adams, Massachusetts", then zoom in and out for maps and create custom driving directions to print out and take with you.

3)  Route 8
Another wonderful north/south drive right through The Berkshires. Route 8 goes beyond Massachusetts of course (north to Vermont, south to Connecticut), but while in Massachusetts it's a road that allows you to get up close with nature and affords a glimpse of the recent past. Otis, Becket, Dalton, Berkshire, Adams...at one time or another, these were industrial towns. A real blue collar no nonsense corridor where you can still see some of the old factories and even some logging still going on between Dalton and North Adams (Route 8A). The northern part of Massachusetts is more stunning because of the taller mountains (Mount Greylock is Massachusetts' highest peak, just under 3,500 feet.). The forest almost starts to take on that boreal feel much like you get in upper Maine or in Quebec. The southern part of the state that Route 8 runs through is more like the southwestern part of Connecticut. The industries are long since gone but many of the people and attitudes remain. However, this real estate market has been discovered and it won't be long till the "old days" are long gone. Many folks ignore Route 8 or don't give it much thought in terms of visiting. But it's a beautiful stretch of road that is sure to capture your imagination in one way or another. Check it sometime but when you go, go slow. There are portions of Route 8 that are dangerous. Most of it is regular old straight road. But certain spots come out of nowhere and sneak up on you. New England is home to the "hair-pin turn" and there are places where you really need to slow down and take it easy. Or you'll find yourself underestimating a turn and coming around it...in the other lane or... into the opposite side forest. Observe the speed limits. I know you have a "car commercial" automobile...the ones that leap over tall buildings, swim under the ocean, scale tall peaks with the top down, grip icy roads like velcro...but I've seen those cars crumbled along the side of road with the driver's face giving off a "I can't believe that just happened to me" look. Unlike other places where speed limits seem to be taken as suggestions, this is a road where you need to pay attention to the speed "suggestion". Great road for cruising, with endless highlights to take in.
Google Map search, "Dalton, Massachusetts", which will put you about mid point along the north/south route, then zoom in and out for maps and create custom driving directions to print out and take with you.

4)  Route 9 (Pittsfield to Northampton)
Though this ride isn't filled with amazing highlights, it's just a nice ride. Whether you're on the Pittsfield or Northampton end, it's a good choice to just get out of the house/hotel and put some distance between you and the hustle and bustle. Along the way you'll definitely cruise through plenty of towns and neighborhoods but they're sparse for the most part and spread out in a way that makes you feel you're much farther out there. From Northampton, the road rises up out of the valley and into some nice forest and open field terrain, then back down again as you approach Pittsfield. Northampton is a college town (Smith College, with Amherst College just a few miles away) and it's a cool place to check out if you haven't been. It's a small town with a Manhattan attitude. All the food, shopping, culture plus a touch of Greenwich Village thrown in. Sometimes the skateboarder, artsy, college kid, granola atmosphere can be a little bit of a cliche' but it also happens to be a nice family town. (I lived there four years...I loved and hated it in equal parts. I loved the surrounding natural environment and all the great outdoor activities within a bike ride, walk, jog, or short car ride away.) Visit nearby Mount Tom for some amazing views of the Hampshire Valley. Or take a ride along the town's wonderful bike path.

Pittsfield is at the other end of the state, and spectrum. Although gentrification (i.e. "money is coming to town") as started in, Pittsfield still holds the character that makes it a unique historical place. Just a couple decades ago it was a blue collar industrial town. Farther back it's roots in the railroad industry are deep and all sorts of things were going on. Herman Melville, author of Moby Dick, grew up in and around. Visit Berkshire's Official Travel Planner to find info concerning Pittsfield's interesting historical facts and places to visit.
Google Map search, "Pittsfield, Massachusetts" or "Northampton, Massachusetts", then zoom in and out for maps and create custom driving directions to print out and take with you.

5)  Stockbridge Loop: Route 7, 102, 41, 23
Many people feel that Stockbridge is the heart of The Berkshire. It's rich in history, culture (opera, theater, symphony, summer Shakespeare), scenic beauty, and centrally located. With this loop you can visit Stockbridge while taking in a very nice ride through The Berkshires. You can create your own variation of this loop depending upon where you are originating from. Take Route 102 west out of Stockbridge downtown area and go towards West Stockbridge. When 102 meets Route 41, take Route 41 south. Eventually Route 41 meets up with Route 23 down by South Egremont. Take Route 23 east towards Great Barrington region. Then back on Route 7 north to Stockbridge.
Google Map search, "Stockbridge, Massachusetts", then zoom in and out for maps and create custom driving directions to print out and take with you.

6)  Route 43
This little route crosses the border in New York off Route 22 and into the northwestern corner of Massachusetts and on over to North Adams. For those coming south via Route 22 it's a nice short cut into the state of Massachusetts and the North Adams/Mount Greylock region. Along the way you'll pass by some of the best state parks in the state. Pittsfield State Forest, Taconic State Park, Clarksburg State Forest (Vermont border), and Mount Greylock. Very scenic and quite peaceful at times. This is a great choice if you're the type who has patience and likes to roll along easy.
Google Map search, "Hancock, Massachusetts", then zoom in and out for maps and create custom driving directions to print out and take with you.

7)  Greenfield, Worthington, Northampton Loop
Start out in Greenfield (or course you can reverse this or make your own loop) which is right off of Interstate 91 and head west on Route 2. Stop in to visit the "Bridge of Flowers" in Shelburne Falls. It's a nice place to take a break and stretch your legs. Then just after Shelburne Falls, go south on Route 112 off of Route 2. It's a beautiful ride through the countryside, passing quaint towns such as Ashfield and Goshen. At Goshen there's a state forest (DAR State Forest) for picnics and hiking. Route 112 joins Route 9 for a bit so go west on Route 9/112 until Cummington where Route 112 veers south again and away from Route 9. William Cullen Bryant Homestead is worth a visit if you're into American authors. When you get to Worthington, go back east on Route 143 as it head back to Route 9 and the town of Williamsburg. Route 9 then heads back to Northampton and meets up with Interstate 91. Go north to finish off the loop back in Greenfield or just head for home if you've had enough for the day. Driving through this region allows you to a nice "quiet" part of western Massachusetts. It gets overshadowed by "The Berkshires" and Northampton region, but it's definitely a scenic drive not to be missed. Nice spots along the way.
Google Map search, "Worthington, Massachusetts", then zoom east for maps and create custom driving directions to print out and take with you.

8)  Mass Pike (extreme western portion)
The Mass Pike?! Yeah...the Mass Pike (Massachusetts State Turnpike). I agree...it's the worst road imaginable east of Holyoke/Springfield. Even Holyoke/Springfield during off-peak hours (rush hour is 7 a.m. - 9:30 a.m. and 4 p.m - 7 p.m.) isn't bad at all. If fact if you hop on the Mass Pike here then head west, it's a beautiful ride. I know you have to pay for it (toll road) but it's not much even if you go all the way to the New York border. But yes, a warning is important...DO NOT GO ANYWHERE EAST DURING RUSH HOUR - Springfield to Boston can be a miserable experience without question.
Google Map search, "Westfield, Massachusetts", or "Lee, Massachusetts", then zoom in and out for maps and create custom driving directions to print out and take with you.

9)  Interstate 91 (above Holyoke)
Interstate 91? Yup, that one too. If you knew your stuff, you'd know that when you get above Springfield it starts to get nice, fast. By the time you come to Northampton, it's beautiful. And it only gets better as you cruise up towards Vermont. A gorgeous ride anytime of year. Stop in and visit Northampton/Amherst area or head up towards Deerfield/Greenfield (for a side trip buzz over to Mount Sugarloaf State Reservation and drive up to the top of picnics and unbelievable views of the Pioneer Valley). Colonial New England, natural beauty, the winding Connecticut River keeping you company, and a bit of the necessary modern world. Put it in the slow lane, put it on cruise control, turn the tunes on or off, and enjoy...you may find yourself wandering well into Vermont. Plenty of scenic rest stops with amazing views so you can stretch your legs and recharge a bit.
Google Map search, "Northampton, Massachusetts", then zoom in and out for maps and create custom driving directions to print out and take with you.

10)  Route 23
Starting out in Great Barrington you head east to take in some wonderful forest scenery along Route 23. At times it'll feel like Vermont, but you're in southwestern Massachusetts not far at all from the hustle and bustle of several different cities (Great Barrington and Springfield). Beartown State Forest near Monterey is one of the best for hiking and camping in the whole state (the Appalachian Trail cuts through and the 1.5 mile loop around Benedict Pond is gorgeous). A few ski slopes, Butternut and Otis Ridge, let you know the mountains are steep enough to handle plenty of packed powder and moguls during winter. The town of Otis still has some logging going on and the timber industry isn't completely gone yet...and it's not likely to vanish anytime soon with all the trees packed in tight. When you get to Otis, go south onto Route 8 and down to the town of New Boston. Then head west on Route 57 in order to create a nice loop back to Route 23 near Great Barrington. Along the way you can stop in Stanisfield State Forest which has 6 small lakes (more like large ponds) where you can swim or fish the trout stocked waters. If you like those scenes where mountains are filled to the brim with timber, this rides for you. Hardwoods dominate and it's good to see that there's a lot of forest left untouched. This part of western Massachusetts is quite rugged looking and always surprises first time visitors with it's natural beauty

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Western Connecticut

1)  Brookfield to Woodbury (Routes 133, 67, and 317)
This drive will take you past historical buildings, picturesque New England villages, farmland, rivers, streams, rolling hills, and into "the antique capital of the Connecticut".  Along the way you can fly fish in a stream, shop for fresh vegetables, visit historical museums, taste wine, enjoy amazing views.  Total time from Brookfield Center to Woodbury should take about 30-35 minutes.  Click here for directions to Brookfield or Woodbury entrance.

2)  New Milford to Litchfield (Routes 7 and 202)
Begin your journey at the green in New Milford. This is a good place to grab some snacks and stretch your legs before venturing northeast on Rt. 202.  Rt 7 and 202 are the same road as you pass through New Milford green.  202 is a main road for local residents but it also happens to be a great scenic road offering lakes, streams, farmland, mountains, art shops, antiques, and quaint New England villages.  Green to green should take about 30 minutes.  Click here for directions to New Milford.

3)  Cornwall to Lakeville (Routes 4, 41, and 112)
Norman Rockwell could have taken this route and spent years painting scenes for his world famous portrayal of American life.  Covered bridges, country roads, dairy farms, small towns, breathtaking scenery are just some of the guaranteed highlights on this route.  Total time from Cornwall to Lakeville should take about 20-30 minutes.  Click here for directions to Cornwall.

4)  Gaylordsville - Dover Plains - Kent (Routes 55, 22, and 341)
If you choose to take this road trip you'll be taken through rural Connecticut and New York. Along this route will be agricultural and historical highlights. Stop by Webatuck Village off Route 55 and watch potters, blacksmiths, furniture makers, glass blowing techniques in this truly unique historical village. See things done as they were over a hundred years ago. Total time will be approximately 45 minutes to 1 hour. Click here for directions.

5)  Candlewood Lake Loop (Candlewood Lake Road, Routes 7, 37, and 39)
Take a ride past New England's largest man-made lake and it's surrounding countryside. Along the way visit classic New England towns like New Milford and Sherman. Total time will be approximately be 1 hour. Click here for directions.

6)  Newtown to Southbury (Routes 34 and 118)
Check out the Lake Zoar region of Connecticut by taking this road trip through Newtown and on over to Southbury. Along the way you go over the Stevenson Dam which provides hydro-electric power to the region and also dams up the Housatonic River to create Lake Zoar. After passing over Stevenson Dam, you'll head onto some backgrounds that quickly become quite rural with that "middle of nowhere feeling". Total time will be approximately 45 minutes to 1 hour. Click here for directions.

7)  Ridgebury to Wilton (Ridgebury Road, Routes 116 and 33)
Riding along the New York/Connecticut border you'll go through southwestern Connecticut and drive past great rural settings and visit colonial towns steeped in history. A relatively short ride, this journey will take about 30 minutes and will encourage to get out of the car and investigate the town center at Ridgefield, which is classic New England. Click here for directions.

8)  Routes 53 and 58
To locals these two routes are well known commuter road linking Litchfield County residents to Fairfield County. During off hours this road trip passes through thick woodlands, lakes, ponds, farmland, and colonial homes. Along the way are plenty of fresh vegetable stands, shops, and a great variety of road side services tailor made for those off on a day trip. Click here for directions.

9) New Caanan/Cross River to Norwalk (Routes 137, 35, 123) Southern Fairfield County is a combination of rustic colonial New England mixed in with modern, fast-paced urban America. Take this drive and you'll see beautiful countryside, historical buildings, exclusive neighborhoods, and a modern Connecticut city with ties to the ancient mariner ways. There are numerous places to stop along the way and investigate or take a break. This trip will take approximately 45 minutes - 1 hour. Click here for directions.

10)  Lake Waramaug Loop
Take Route 202 to New Preston, Connecticut which is about halfway between New Milford and Litchfield. At New Preston, follow the sign to Lake Waramaug. A slow drive through the town center eventually leads you right up to the lake. At the stop sign, go left onto West Shore Road. This winding, twisting road follows the bank of the lake for several miles and eventually winds up at Lake Waramaug State Park where you can picnic, fish, rent a paddle boat, or campout. Beyond the park, the road comes to a 3-way intersection. Go right and stay with North Shore Road and eventually you will go past The Inn on Lake Waramaug. This road ends back at the main road, Lake Shore Road (or Route 45 to non-locals). Take a right and go south to get back to where you started. This loops takes your all the way around this small lake, right along the shore the whole way. PLEASE DRIVE SLOWLY AS THIS IS A BEACH COMMUNITY AND USED BY A LOT OF PEOPLE. CHILDREN, PETS, TOURISTS, RESIDENCE NEED TO CROSS THE ROAD TO GET TO THE BEACHES. BE RESPECTFUL AND BE POLITE...MOST OF ALL BE CAREFUL. Google Map search, "New Preston, Connecticut", then zoom in and out for maps and create custom driving directions to print out and take with you.