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Guide to a New England Fall Vacation

autumn leaves in new england
Allianz - autumn leaves in new england

New England's wealth of historical sites, charm and natural beauty make it a great destination for a vacation at least nine months out of the year. It abounds with attractions such as covered bridges, lighthouses and old country stores that beckon visitors to stop and explore. However, a trip during fall when the vibrant flame of foliage dazzles the eye will leave you completely enchanted with this unique area of the country. Here is an itinerary that includes points of interest you won't want to miss, and don't forget your travel insurance to take care of the unexpected on your journey.

General Tips

Although the suggested travel plans deal with specifics, some general guidelines apply:

  • The itinerary includes some freeways, but you should plan on spending most of your time traveling the highways and byways. These roads offer much better views of the foliage and towns. In fact, too much freeway travel will cause you to miss the true New England experience.
  • When looking for lodging in villages and rural areas, choose country inns over chain hotels. The inns have character and personality that will add immeasurably to your trip. Some inns are a decorator's dream, but even the plain ones have features you will enjoy.
  • The itinerary suggests places to eat, but sometimes unassuming roadside stands can have tasty food. In addition, if your inn is one that provides dinner, the meal is sure to be memorable.
  • Fall is harvest time in New England, and the region celebrates its apples, pumpkins and cranberries through an array of festivals. The events are delightful affairs that include baking contests, pie-eating contests and more. Be sure and stop if you happen across one of these festivities.

Day One: Connecticut

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A good place to begin your journey is a region of Connecticut known as "the quiet corner." Route 169 from Lisbon to Woodstock is a visual feast of gently rolling hills, historic churches, apple orchards and village greens. Try one of the hiking or biking trails just off the road, or you can tour the Prudence Crandall Museum in Canterbury. Suggested lodging is the Golden Lamb Buttery in Brooklyn, an estate in a lovely setting where you can go on a hayride as well as have a fine dinner. If you're in the mood for a snack when passing through Woodstock, drop into Soleil and Sons Bakery for an irresistible selection of home-baked goods.

Day Two: Plymouth, Massachusetts

Allianz - Plymouth, MA

At Woodstock, take US 44 west to Plymouth, Massachusetts. The main attraction is Plymouth Plantation, a fascinating recreation of the small community built by the Pilgrims. It involves actors in period dress who portray the people who actually lived there. Visitors can ask them questions, and they will reply in character. You may want to stay at the Mirbeau Inn and Spa, a lodging with an on-site restaurant and beautiful gardens.

Day Three: Boston, Massachusetts

Allianz - Boston

After Plymouth, move on to Boston, where the historic sites of the American revolutionary period will inspire you. These places include the Freedom Trail, Old North Church, Paul Revere's house, the Boston Tea Party Ships and the USS Constitution. Suggested lodging is the Harborside Inn, which is in a perfect location. For breakfast, try Mike's City Diner, a '50s-style eatery with excellent food.

Day Three: New Hampshire

Allianz - New Hampshire

Take I-93 north to Lincoln, New Hampshire, the starting point of the must-see Kancamagus Highway. This is a breathtaking 32-mile stretch of scenic vistas on Route 112. It ends in Conway, where attractions include the Settler's Green Outlet Village, Mount Washington Observatory Weather Discovery Center and the Conway Scenic Railroad. A lodging suggestion is the Wyatt House Country Inn, which offers a superb breakfast. Dine at May Kelly's Cottage Restaurant, where you can eat on the terrace while savoring a view of the river and mountains.

Day Four: Southern Maine

Allianz - Portland, ME

Another road that affords beautiful foliage views is Route 302 from Conway, New Hampshire to coastal Maine. You'll pass several villages before you get to the seaport of Portland, where you can browse through shops, museums and galleries. Another option is to take a day cruise and relish the salty air. The Pomegranate Inn is a highly rated bed and breakfast that has an elegant, romantic ambiance. Portland also has a reputation for being a foodie's delight, so you may want to try restaurants like The Back Bay Grill or The Green Elephant.

Day Five: Mid-Maine Coast

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In Portland, get on Route 1 and head north to see more coastal towns. Stop at Wiscasset, known as quintessential Maine. Move on to Boothbay Harbor, a town noted for water sports and whale-watching cruises. Next, travel to Rockport, where you can tour craft shops and admire the picture-postcard views. Rockport waterfront lodging suggestions include the Strawberry Hill Seaside Inn or Ledges by the Bay. For a special evening, dine at La Bella Vita, an Italian eatery with a view of the harbor and bay.

Day Six: Vermont

Allianz - Vermont

Take US-2 east from Rockport to Shelburne, Vermont, where you can tour the Shelburne Museum, an amazing depository. Afterward, drive the short distance to Middlebury, a cozy town that is home to two covered bridges, the Vermont Folklife Center and the Lake Champlain Maritime Museum. Suggested lodgings are Inn on the Green or Swift House Inn. Have lunch or dinner at American Flatbread, a popular eatery that has received rave reviews.

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