Lover’s Lane

  • Connecticut + 3 more
  • Self Drive Ideas
  • 9 Days
from  £1,125pp
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Discover New England staying in iconic Inns and hotels

A Free Personalised Road Book is included as standard with our Self Drive itineraries. 


Please note: – This is a suggested itinerary only and is intended to give an overview of what is possible. All of our holiday itineraries are fully customisable and can be tailor-made to suit your own individual requirements.  If you would like to start in a different destination, use specific hotel accommodation, include an extra night here, a side-trip there and/or include tickets to an event please let your Discover North America travel specialist know. They’ll also book you the best value flights to ensure a seamless holiday experience.



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Days 1 – 3 Boston – Meredith (99mi/160km)

Just 1.5 hours north of Boston is the southern lakes region of New Hampshire. Summer brings band concerts to the common, popular musicals to the Playhouse, festivals, and fairs. Winter activities include skiing, snowshoeing, cross-country skiing, and snowmobiling. Enjoy two nights at the charming Inn at Pleasant Lake, a beautiful waterfront property offering spacious rooms, award winning gourmet meals, and access to a wide array of activities such as kayaking, hiking and golf.

Days 3 – 5 Meredith – Goshen (81mi/130km)

Wind along scenic roadways to the Shires of Vermont, a collection of perfect small towns complete with village greens, whitewashed steeples, quaint B&B’s and covered bridges. There are outdoor activities, from fishing and golfing to alpine skiing, and shopping is easy to do with more than ample antique, handcrafts, and designer fashion outlets. Two nights will be spent at the magnificent Blueberry Hill Inn, a charming 1800’s inn.

Days 5 – 7 Goshen – Stockbridge (68mi/109km)

The Berkshires hold a treasure trove of sites and attractions. The world renowned Clak Art Institute and Summer Stock Theater, the Norman Rockwell Museum, Tanglewood, summer home of the Boston Symphony and much more. All these sights are a short drive from the Red Lion Inn in Stockbridge, home for the next two nights. Romance is alive in the warm, cozy sophisticated guestrooms.

Days 7 – 9 Stockbridge – Martha’s Vineyard (187mi/301km)

Drive east to Cape Cod. Passengers and vehicle board the ferry for a 45 minute ride to Martha’s Vineyard. Explore the island’s six independent towns. See the iconic lighthouse on Gay Head, the colourful gingerbread houses in Oak Bluffs and stroll through architecturally elegant Edgartown. On Day 9 take the return ferry to Woods Hole and then it’s just 1.5 hours back to Boston.