Five Breathtaking New England Road Trips

High above the Lake Champlain Islands in Vermont. / Photos by Dominic Casserly

Nothing beats New England in the fall. White-steepled churches engulfed in searing red and gold. Rolling hills suddenly aflame with color. Twisting back roads covered in cartwheeling leaves. For a few short weeks each year, the scenery is grand, the temperature’s just right, and the open road beckons. To help you make the most of this driving season, we asked automotive writer Clifford Atiyeh to map out five of the region’s best journeys and pick out the perfect vehicle for each jaunt.

Massachusetts: Northampton to Dover

Route:
A ramble through western and central Massachusetts, with stops in Northampton and Worcester; the best back road in the metro Boston area.

Distance: 111 miles   |   Car: Mercedes SLK 250

Massachusetts to New Hampshire: Beverly Farms to Holderness

Route:
An easy trip that turns into a driving workout; outrageous views en route to New Hampshire’s Lakes Region, with stops in Newburyport and Meredith. 

Distance: 135 miles   |   Car: Bentley Continental GT 

Maine: Kittery to Yarmouth

Route:
A leisurely cruise up the Maine coast, with stops in Kittery and Portland; a visit to the cliffs where Winslow Homer once painted.

Distance: 95 miles   |   Car: Rolls-Royce Ghost

Vermont: Lake Champlain Islands to St. Johnsbury

Route:
A jaunt across islands and through backcountry Vermont, with stops in Burlington and St. Johnsbury; a hunt for a covered bridge in Cabot; and the state’s best hidden beach.

Distance: 124 miles   |   Car: BMW 640i Gran Coupe

Connecticut: Killingworth to Lakeville

Route:
A zip through inland Connecticut, with stops in Meriden and West Cornwall; a stay in a Winvian cottage; and a lap around Lime Rock Park.

Distance: 85 miles   |   Car: Subaru BRZ

WEB FEATURE:

Get Your Car in Road Trip Shape
Tips and things to check before you hit the open road.