Come explore the Shires of Vermont with these rides...

Come explore the Shires of Vermont with these rides...

The Shires of Vermont provides one of the best motorcycle riding areas in all of the Northeast!

With the fresh air of Vermont and surrounding locations, the rolling hills of the Shires and blue skies for miles, the view & the stunning scenery is best appreciated when in the seat of a motorcycle.

From that window-less seat you can enjoy the beautiful country, forests, rivers, covered bridges, little towns and mountain views.  For your pleasure and to provide you with helpful, must-drive routes, we have put together some amazing rides that start and finish in the Shires of Vermont.

There is so much to see and so many wonderful shops to stop at that we can’t mention them all but we will highlight a few suggestions along your route as well.

Ride safe and enjoy your ride! Please share your stories with us at info@bennington.com


White Creek NY Route 68 loop 26.7 miles // 45 minutes

Route 68 is a beautiful ride that highlights the farm country of Vermont and New York. Enjoy the rolling hills and twisty roads. Return back to Vermont on Route 22/67. 

Lake George, NY loop | 132 miles // 3 hours

The queen of the American lakes and the Adirondacks of upstate New York. It's home to Americade and there are three covered Bridges can be found along this route as you are leaving town.

Rick’s Tavern & Curtis BBQ  | 139 miles // 3 hours 30 minutes

This is a beautiful ride through the little towns that make Vermont so special.

You will enjoy Rt 7A to Manchester, Route 30 South which will bring you past the W. Dummerston Covered Bridge into Brattleboro and Route 5 North which will bring you right to the famous Curtis Bar-B-Que. Your Return trip to Bennington will be on Route 9 West over 2 scenic mountains. Just 12 miles from Brattleboro is The Southern Vermont Natural History Museum. Also home to the 100 Mile view and Hogback Mountain Gift Shop.

Route 22 Granville NY/Dorset Quarries | 91.7 miles // 2 hours

This is a beautiful ride through the little towns that make Vermont so special.

You will enjoy Route 7A to Manchester, Route 30 North where you will find The Dorset Quarries.

Marble carved from the site was used to build the New York Public Library, the Montreal Museum of Fine Arts and the Harvard Medical School buildings. The quarry shut down around 1917, and when a stream filled it with water it became a popular swimming spot.  

Route 149 will bring you into New York and you will enjoy Route 22 and Route 67 back into Vermont.

VT/MA/NY | 43.7 miles // 1 hour

This ride will bring you into three states and give you a great ride in a short amount of time. You will travel on Route 7 south into MA which will turn into Route 2. You will turn onto the Taconic Trail Route 2 west which you will bring you over the mountain and into NY.

In Petersburg, NY you will travel on Route 22 until the Stewart’s Shop in Hoosick, NY. Turn right onto Route 7 and follow it back into Bennington.

Vermont Country StorE | 107 miles // 2 hours 30 minutes

Traveling Route 7A north into Manchester where you will get on Route 11.  In Londonderry watch for signs for Route 100 North

Route 100 is known as one of the best  roads to travel the state if you want a scenic country ride.. The Vermont Country Store is only 5 miles on Route 100 The address is 657 Main Street Weston, VT.  Step back to simpler times and take a stroll down memory lane while shopping for practical or hard to find items.

Your return route back to Bennington will be on great country roads through the mountains. You will see beautiful rivers, enjoy windy twisty roads and see the scenic sights that make Vermont so special. Make it a day trip and bring your camera because you will love the scenic views.

Battle Monument - Route  346 - Route 22 | 31.6 miles // 46 minutes

Visit Vermont’s tallest structure, built to commemorate a pivotal Revolutionary War battle that changed the course of American history before heading south on Route 7.

In Pownal you will follow Route 346 which will show you some nice farm lands on a twisty road with scenic views.Shortly after you cross the into NY Route 346 will end and you will go right on Route 22 until it joins with Route 7. The Stewart’s Shop is a great place to gas up or use the facilities.You will travel East on Route 7 back to Bennington.

Brattleboro Route 9 - Route 30 | 111 miles // 2 hours 44 minutes

This is a great ride. It could get chilly in the mountains so bring an extra layer.

Rt7A into Manchester is a scenic ride through a few small towns. Rt 30 east will bring you the long way into Brattleboro, but the ride is worth it. The Whetstone Brewery is a great place to eat and have a hot or cold beverage. The Whetstone overlooks the Connecticut River and is a local favorite.

Your return route with be Rt 9 West which is about 40 miles of scenic twisty roads over two mountains. There is a scenic pull off at the top of Hogback Mountain that gives you a 100 mile view.

Long Trail Brewery | 170 miles // 4 hours

If you are looking for an all day ride this is it. Your ride can be shortened if you do not have the time to do the scenic route on your return. It is 1 hour 45 minutes from Bennington on Rt 7North and Rt 4 east.

The Long Trail Brewery is a favorite amongst locals and travelers because of the great food and fresh brewed beer that is brewed on the premises.

The scenic ride home is 70 miles on Rt 100 south which is known for its great riding because of the twisty roads that often follow rivers or border small lakes and ponds.

The higher elevations will have a  drop in temperature so be sure to bring an extra layer of clothing.

In Wilmington you will get on Rt 9 West to bring you back to Bennington.

313 Cambridge/Arlington Loop | 48.1 miles // 1 hour 7 minutes

This ride is a favorite for our locals. It’s a quick ride when you don’t have much time but want to experience a great ride.

Rt. 67 will bring you into NY and Rt 22 will bring you into Cambridge.

Rt 313 is a great ride through some old farm properties and along the famous Battenkill River. In Arlington you will get on Rt7A south to return to Bennington