Step Back in Time ... Our Unique Getaways

Unique New England Getaways - Classic Cars and BywaysAs a Classic Cars and Byways customer you can enjoy our getaways at no extra charge.

You'll have detailed directions that will help you make the most of your time and lead you to the most scenic, fun-to-drive roads in the area. Each of our getaways features a unique historic, cultural or just plain fun aspect of the countryside around Boston. If you also want to explore on your own, you’ll have a laminated map of eastern Massachusetts that highlights the quieter roads favored by cyclists – a good guide for the classic car driver!

"What a great way to celebrate my husband's birthday.  We tooled around west of Boston and made great use of your cycling maps.  It was very helpful in a few places where the roads got too congested or too bumpy -- we just consulted the map and took another route. We passed the Gropius house and the DeCordova Museum, although Jamie wasn't willing to get out of the Speedster and dawdle -- a good sign!  Thanks so much!"

--Gioia Perugini


Add a picnic to your Getaway!

Classic Cars and Byways

To provide you with a fully stocked picnic hamper, we’ve teamed up with Baker’s Best Catering – a local gourmet caterer and 11-time winner of Boston Magazine’s “Best of Boston” award.

When you make a reservation, ask us for more details about this enhancement to your Getaway!






Wine Lovers' Getaway

Classic Cars and Byways - Plan a Getaway tour to a winery
Beginning in Newton, Massachusetts, our route leads you through horse country in the Boston suburbs of Dover and Medfield and along the byways of southeastern Massachusetts to connect with the Coastal Wine Trail in Rhode Island.

The wine tour itself leads you to five varied vineyards. Each vineyard offers tasting and tours of its facilities.



The back roads in this area are stunning, complete with long vistas from hilltops to the sea, isolated farmhouses, twisty turns and great spots for picnics.

This tour can be combined with stops in Newport and Providence


Historic Homes and Byways

Historic Homes and Byways - Classic Cars and BywaysThis tour leads you to a careful selection of historic residences that provides a three-century guide to residential architecture of New England.

Starting at the Cooper-Frost-Austin house in Cambridge (the oldest house in the city) built in 1681, the tour traverses back roads to the north of Boston, with stops at the similarly aged Broadmor house in Saugus (1687) and the Coffin House in Newbury (1678). In Gloucester the tour stops at Beaufort, a wonderful example of a summer cottage of the gilded age, before returning south to Lincoln to visit an earlier time at the Codman house (1790) and a classic of mid-century modernism, the Gropius house (1937).


Book Lovers' Odyssey

Historic Homes in New England - Classic Cars and BywaysThe Book Lovers' odyssey tours through the villages of the Pioneer Valley, likely the most author-saturated, book-cherishing, literature-celebrating place in the country.

You can visit any number of unique, independent bookstores and libraries with specialties for every book lover – mysteries, romances, and local history. In addition, more than 100 published authors call this part of New England home, meaning there is always a rich and varied selection of authors talks, book signings, and lectures along the way.



Summer Stock Special

Getaway to Summer Stock with Classic Cars and BywaysThe heyday of summer stock took place from the 40s to the 60s, when the "straw hat circuit" provided a training ground for the country's best actors and great, cheap entertainment for millions of vacationing East Coast urbanites.

Plays and musicals that had closed during the previous season on Broadway would hit the circuit; aspiring youngsters (Jane Fonda, for example) and veterans seeking a more bucolic stage would entertain.


Some of the original venues such as the South Shore Music Circus in Cohasset and the Cape Cod Melody Tent in Hyannis now specialize in concerts.

Others -- the Cape Playhouse in Dennis (America’s oldest summer theater) and the Monomoy Theater in Chatham (summer home for 51 years of the Ohio University Players) -- offer a variety of theater treats. You'll find the Cape's back roads equally entertaining.


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