The Perfect Itinerary for Your 2017 Fall Road Trip Through New England

It has been said that there is no where better for Fall travel than New England and I would have to agree. Road tripping through the brightly colored leaves in New England should be on everyone’s bucket list. The itinerary planning can be a bit overwhelming. It can be challenging to create one that allows you relaxation and leisure without missing out on things while you are there. This itinerary will allow just that, plenty of time to leisurely explore but still well planned so that you can experience all that New England has to offer.

Day 1-Thursday, October 12
Catch an early flight Boston. You will want to arrive as early as possible to maximize your time. Pick up a rental car from the airport (make sure you book it ahead of time and get one with unlimited miles) and spend the day exploring Boston.

Some suggestions for your day in Boston
Everything on the Freedom Trail
The Original Cheers Bar
Union Oyster House 
(America’s Oldest Restaurant)
Drink a pumpkin beer in a cozy Irish Pub
Sam Adams Brewery Tour
Bell in Hand Tavern (America’s Oldest Tavern)
Tour Fenway
Go to the Bleacher Bar
Eat an original Boston Cream Pie


There is so much to see and do in Boston you will not have any trouble filling your day. However, don’t lose track of time too much because next on the list is Salem and you will want to make sure you get there before dark (although it is a blast when it does get dark). Salem is about a 30 minute drive outside of Boston. Upon arrival you will quickly realize this town known for it’s witch trials celebrates Halloween all month long. A month long celebration called Salem Haunted Happenings will provide you with plenty of activities for your evening. Along with that, if you are a Hocus Pocus fan (who isn’t), you can visit sites that were used in the film. Find a list of those here. You can follow the red line through Salem to see all of the historic locations including the cemetery, witch house, and witch museum. Book a hotel close to Salem or somewhere in route to the next days destinations.

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Day 2-Friday, October 13
Start your day by beginning route toward the charming small town of Keene, New Hampshire. If you begin in Salem, Keene is about a two hour drive. There is a lot to see and do along your two hour drive to Keene. Stop in and explore the small towns you drive through, take time to visit the pumpkin patches and farms you travel through, visit the Little Women house, covered bridges, etc. Use to put in your route and find attractions along the way to pick stops that appeal to you.

From Keene continue North, about another two hours, to the Stowe and Waterbury area of Vermont. Waterbury is home to the famous Ben and Jerry’s Factory. You can take a tour and even visit the flavor graveyard where they keep all of the flavors that are no longer being made. You will be in Vermont for the night and part of the next day before traveling back into New Hampshire the next day. Some things you have to do while you are in Vermont are: eat apple cider donuts, drink fresh apple cider, visit a cheese farm, visit a maple syrup sugar house, take a foliage drive and explore, stay somewhere cozy and enjoy the views.
Some suggestions for your time in Vermont
Drink apple cider and eat donuts at Cold Hollow Cider Mill
Spend some time at a pumpkin patch and take a hayride
Pick apples at an apple orchard
Taste maple syrup at Sugar Bush Farm
Try famous Vermont cheddar cheese
Visit a year round sugar house at Morse Farm
Stay at a cozy bed and breakfast like Homeplace
Take a scenic drive through the foliage
Stay in a cabin with a great view like this

IMG_0025 pumpkin patch

Day 3-Saturday, October 14
The next day you will spend your time finishing up your stops in Vermont and enjoying your drive to Laconia, New Hampshire which takes about 2 and a half hours. Laconia is home to the New Hampshire Pumpkin Festival. This 2 day festival truly encompasses what Autumn is all about. The whole town is filled with over 20,000 lit jack-o-lanterns, live bands, food trucks, etc. The festival goes from 12:00-8:00, you will want to be there a little before dark and stay into dark so that you can see the town but also see the pumpkins when they are lit.


That night you can either stay close by or cut a little morning drive time out by heading toward Freeport, Maine which is about a two hour drive from Laconia.

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Day 4-Sunday, October 15

The next morning you will want to get an early start so that you have plenty of time to explore the coast of Maine. The first stop will be in Freeport, Maine and you will work your way down the coast from there. While in Freeport make sure to take a peak at the McDonalds and to visit the L.L.Bean Flagship Store. As you work your way down the coast some suggested stops are: Portland, Old Orchard Beach, Kennebunkport, and Ogunquit, as well as Portsmouth, New Hampshire (all are less than half an hour apart). Make sure you eat a lobster roll at some point and stop by the famous Portland Head Light House.

The time of your departing flight will determine where you should book your hotel for the night. If you have an early morning flight you will want to get as close to Boston as you can. If you have a flight later in the day or into the evening you can spend more time on the coast and book your hotel there for the night (which would be my suggestion if flight times are an option). If you do have time to stay on the coast I highly recommend the Old Village Inn in Ogunquit. I cannot speak highly enough of the owners, they are so welcoming. If you do not get to stay there at least take time to stop in for a drink at their cozy bar or have a meal at the restaurant.

Image result for portsmouth new hampshire fall
Day 5-Monday, October 16
Try to book a flight later in the day so that you can spend as much time as possible on the coast on Sunday and even into Monday morning.

What to do before you leave
√ Rent a car with unlimited miles from early Thursday to late afternoon on Monday
√Book a hotel close to Salem, Massachusetts for Thursday night
√Book a cozy place to stay near Waterbury, Vermont for Friday night
√Book a hotel between Laconia, New Hampshire and Freeport, Maine for Saturday night
√Book a hotel between Portsmouth, New Hampshire and Boston, Massachusetts for Sunday night

Vagary Travel is happy to help design and book your New England adventure and I am happy to answer any questions you have about any destination.
Contact me anytime!

Links to pictures that are not my own:
tea party
green dragon
witch house
pumpkin patch
cider mill
vermont pumpkins
ll bean
new hapshire

2 thoughts on “The Perfect Itinerary for Your 2017 Fall Road Trip Through New England

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