Choosing Your Stops in New England – The Best Type of Dilemma to Have

The toughest thing about a New England road trip is deciding where to go. The choices are endless and options appealing to every type of traveler abound. Whether your taste is city break or “get away from it all”, a family bonding session, or a much needed romantic break, this collection of 6 very special states has something for you.


The first decision to make is when to go. Anyone considering a trip here knows that autumn is a very special time but spring and summer are typically accompanied by excellent weather and plentiful activities including renowned festivals. Winter can offer amazing scenic opportunities but snow and ice storm can make driving unpredictable. If crowds and traffic jams are not your thing, you may wish to avoid certain parts of New England, particularly around Boston and Cape Cod during the summertime and well known fall foliage routes during the autumn.

New England consists of six U.S. states, many with histories as early as America herself. Four of the six were members of the 13 original colonies and all, with the exception of Maine, joined the Union in the 18th century. This longevity provides travelers with not only natural beauty and entertaining events but also a long and rich past based on strong roots in American history.

When meeting most New Englanders, particularly those from small towns, it becomes evident quite quickly the friendliness and coziness which is commonplace in New England. With the exception in some big cities, New Englanders are small town at heart and newcomers to the area enjoy fantastic hospitality. Expect to sit down for a while when arriving at your B&B or inn – your host or hostess is likely to want to pull up a chair and share with you the history and/or the offerings of Marblehead, MA or Castine, ME.

The Locations:

The number of places to choose to visit within New England are plentiful. Boston is a must-do and any visitors would be remiss to forego this historical powerhouse of the region. Additional options are given below and can be used to supplement your itinerary based on you and your family’s or travel partner’s specific interests.

Most visitors arriving in New England will fly into Boston’s Logan Airport, explore the city, rent a car, and be on their way to their next destination. This is one option and it does allow you to explore the city while you are fresh and have not yet been scarred by the traffic which is common throughout New England. Another consideration would be to plan to be in Boston on the weekend and hit the road during the week to, hopefully, avoid some of the traffic gridlock common in places like Cape Cod. .

The main purpose of your visit to Boston is not ONLY to catch a Sox or Patriots game although these are must do’s if you are in Boston during their game seasons. It is to get a first-hand account of key American historical events – where they occurred. The Boston Harbor must be visited as the site of the Boston Tea Party. The three mile long Freedom Trail takes you to 16 key historical sites including the Boston Commons, Paul Revere’s Home, and the King’s Chapel.


Additional Locations

Cape Cod, MA – A must-do in New England. Stay in one of the countless B&B’s Tall Ship, Honeysuckle Hill, or Lamb and Lion. Rent a bike in Nantucket or Martha’s Vineyard.


Northeast Kingdom, VT – Visit the numerous sugar shacks in winter/early spring to see how maple syrup, maple sugar candy and other delightful treats are made. Sample the products and take some back home with you.

Block Island, RI – Avoid the crowds at nearby Newport and instead enjoy this out of the way island retreat. With sandy beaches and excellent lobster houses, Block Island can be reached by ferry from Point Judith.

Mystic, CT – Get into the nautical mode in Mystic and enjoy the coastline, aquarium, and special events held on ships. Mystic is a true New England seaport village.


Vermont Leaves and Covered Bridges – It is virtually impossible to narrow down specific towns within Vermont to target in order to enjoy the fall foliage and covered bridges. Throw out your itinerary and just drive. Stop when it suits you and get back in the car when you have had enough – if that moment ever comes.



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