One Week New England Roadtrip

by Charlie - Where Charlie Wanders

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One Week New England Roadtrip

It is possible to have an incredible time in New England, even if you have limited time to spend there. This post covers how to have an epic one week New England Roadtrip and maximise the amount of time you have to spend there. Going on a roadtrip is one of the best ways to experience this part of the USA. It gives you the freedom and flexibility to get to some of the more off the beaten track locations and well as throwing in a few unplanned stops. Plus means you get to see some pretty epic views!

One Week New England Roadtrip Itinerary at a glance

Day 1 – Arrival / Boston

Day  2 – Brattleboro / Rockingham / Newfane

Day 3 – Quechee / Woodstock

Day 4 – Waterbury / Stowe

Day 5 – Burlington / Stowe

Day 6 – Kennebunkport

Day 7 – Rockport

Day 8 – Salem / Depart

image of map showing one week New England Roadtrip itinerary

Arriving into New England

The easiest and most convenient airport for New England is Boston Logan International Airport. This is one of the USA hubs, so there are plenty of flights daily from multiple locations all over the world.

From the airport terminal you take a bus to the car hire centre, which is open 24 hours. This is really handy if your flights arrives later in the evening.

One Week New England Roadtrip in detail!

Day. 1 – Arrival / Boston

How you spend this day really depends on what time of day you arrive in to New England. If you have an earlier flight, it would be a great opportunity to head into Boston for a spot of sight seeing. However, if the flight lands later in the evening, then the best thing to do once you have collected the hire car is to head slightly out of the city.

Driving even half an hour or so North means the next day you are best placed to head straight out of Massachusetts into Vermont, and don’t get caught up in any city traffic. By leaving the city in the evening you avoid any Boston traffic jams that might occur during the day. The hotel prices are also a little cheaper than in central Boston.

Take a look at South Burlington, MA for a good distance out of Boston. If you are looking for something very functional, as simply a place to crash for the night, try Sonesta Suites Boston. Click HERE.

The hotel isn’t amazing, but it is in a good location.

Day 2 – Brattleboro / Rockingham / Newfane

Leave Massachusetts first thing and drive through New Hampshire into Vermont.

Start the day by heading to Brattleboro. The drive should take just under 2 hours. This town is located literally just over the border from New Hampshire into Vermont – cross a bridge and you are in Vermont. This is a nice town to stop and have a quick wander around, but perhaps not worth staying overnight in. When you arrive in Brattleboro head to Duo for some brunch. They have a great selection on their menu, including cider pork benedict or pancakes for your first taste of Vermont maple syrup!

Upon leaving Bratteboro there a number of places to head to continue with the New England Roadtrip!

Start by heading to Grafton Village Cheese to sample some local cheese, slurp on a maple creemee and take a look at the cute little farm buildings.

image of Grafton Village Cheese which is a stop on a one week New England Roadtrip

From there go via the town of Rockingham for a wander around. After this stop at Vermont Country Stores to spend all your dollars on things you didn’t even know you needed, but you absolutely did. It is also so traditional inside, selling all sorts of local goods. So worth a look even if you don’t want to splurge.

image of Vermont country store

Following this head to your overnight stop in the town of Newfane. This little town is incredibly picturesque, but there isn’t a huge amount to do as it isn’t very large. Therefore the best time to arrive would be late afternoon, early evening. This way you can check in, relax and have a wander of the town before going out to enjoy dinner.

Total driving time: 3 hours ( or 2 hours if you choose not to visit Rockingham)

Where to stay: Four Columns

Where to eat: Fat Crow

Day 3 – Quechee / Woodstock

Set off from Newfane in the morning and make your way towards Woodstock, your overnight destination. There are, of course, a couple of places to check out on the way!

Firstly Sugar Bush Maple farm where you can try the local cheese made here, as well as seeing how maple is tapped.

After leaving the farm head towards Quechee. This isn’t a huge place, however there are a couple of places to check out when you are there. Upon arrival head to the Quechee Gorge bridge for outstanding views down the valley from quite the height. Then take the hike down to the bottom to see the river and look back at the bridge.

image of the green and orange trees at Quechee Gorge, Vermont

After you have visited the gorge Quechee Gorge Village is worth a stop, as it has lots of little shops to check out. Including the most enormous antiques shop you might ever possibly see in your life. If you are hungry there is also a diner housed in an old rail carriage, which is interesting!

Just after lunch head towards Woodstock, it is such a pretty town therefore you are going to want to make sure you have time to explore. Check out the traditional shops including FH Gillinghams and Sons. Plus, there is a Vermont covered bridge to be found here!

image of the centre of Woodstock, Vermont a must see on a one weekend New England roadtrip

Total Driving time: 1 hour 45 minutes

Where to stay: The Shire, Woodstock

Where to eat: Worthy Kitchen

Day 4 – Waterbury / Stowe

Today set off from Woodstock in the general direction of Stowe. Stowe itself is a lovely little town, so this one week New England roadtrip itinerary actually has a two night stop in the town. However, before you arrive there are a couple of places to check out on the way!

The location of these are in Waterbury. First, how can any trip to New England or Vermont be complete without visiting the iconic Ben & Jerry’s factory? Vermont is the birth place of this brand and you can take a tour of the factory along with a sample of one of the flavours.

image of green and blue Ben and Jerry's van with cows in Waterbury, Vermont

After filling up on ice cream, head to potentially one of the best stops in Vermont – Cold Hollow Mill ! Here you can munch on fresh doughnuts as well as taste delicious cider straight from the mill. There is also the most amazingly fresh apple juice to try. Plus a great gift shop!

Afterwards head towards Stowe to have a wander and get to know the town.

image of Stowe church against fall foliage in Vermont

Total driving time: 1 hour 30 minutes 

Where to stay: Little River Inn

Where to eat: Doc Ponds

Day 5 – Burlington / Stowe

Having stayed overnight in Stowe you are in an excellent place to head out to see the city of Burlington in the morning. This city isn’t the capital of Vermont, but is the most populated city of the state.



It still isn’t a large city, but Church Street is worth taking a look at. Full of independent shops and cafes, its great to wander down and get a feel for the place. Also check out the famous Lake Champlain. The chocolates named after this famous lake are also worth sampling!

image of the blue and still water of Lake Champlain in Burlington, Vermont

In the afternoon head back to Stowe, as you will want to take some time to get to know this town a little better. Take the walk from behind the church towards the upper part of the town, for some beautiful views across the town. Stowe also has a ski resort to explore, so if you have time head to the other area of this town. As well as taking a ride on the gondola! Make sure you check out a covered bridge or two! Emily’s bridge, which she apparently haunts, or the red covered bridge at Cole Hill Road.

image of Emily's Bridge in Stowe, Vermont with fall foliage

For even more covered bridge inspiration: Covered bridges in Vermont you need to see!

Day 6 – Kennebunkport

Today is the day to leave Vermont and head into Maine! This will be the longest day driving, but worth it for the coastal scenes. The quickest and most direct way to get to Kennebunkport is on the I89 and then the I95. However, instead of taking the I95 take the coastal highway – U.S Route 1 for some amazing views. You also drive through some very pretty villages, so you might be tempted to take some stops to have a look around and stretch the legs.

Leaving Stowe early morning is recommended as this means you can arrive in Kennebunkport in time for lunch. And there is only one place you need to head to – the Clam Shack for the famous lobster roll. Even recommended by George W. Bush.

image of the Clam Shack in Kennebunkport, Maine

Afterwards just take a wander around the town, browse the shops – definitely check out Minka, eat the delicious tiny doughnuts at Satellite Doughnuts, try the local gin and watch the tide come in under the bridge.

image of chocolate and pretzel Satellite Doughnuts in Kennebunkport, Maine

Total Driving time: 3 hours 30 minutes (4 if you want to drive through White Mountain National Forest).

For more information on what to see in Kennebunkport, take a look at this post:

14 things to do in Kennebunkport, Maine

Where to stay: King’s Port Inn

Where to eat: Baston River – for food and for the local gin!

Day 7 – Rockport

Before leaving Kennebunkport head to Gooch’s Beach to dip your toes in the ocean! It’s a long stretch of beach; amazing when the sun is out. Finally take a quick drive by President Bush’s house – obviously can’t get close!

image of Where Charlie Wanders splashing in the sea on Goochs beach, Kennebunkport in Maine on a one week New England roadtrip

After leaving Maine on the final full day in New England head towards Boston and return to Massachusetts! Bearskin Neck and Rockport is the absolute gem of a place to spend your final night. A beautiful town; so easy to wander around. For rom com fans – it is where The Proposal, featuring Ryan Reynolds and Sandra Bullock, was filmed.

image of the purple and red fudgery in Bearskin Neck, Massachusetts

Home to the famous Motif #1; a fishing shack located on Bradley Wharf.  Said to be the most painted building in the world; surrounded by lobster cages, it does have a traditional feel.

To note-  if you come out of season, a lot of the shops have closed for winter. However in summer through to the end of September most are open.

Worth mentioning that it is hard to buy alcohol. Not all the restaurants have licences and only one shop sells it. This is due to to Hannah Jumper whose ‘Hatchet gang’ raided Rockport establishments that sold alcohol, back in 1856. As a result of this Rockport became a dry town until 2005 when residents voted that alcohol can be sold in restaurants if having a meal. It wasn’t until 2019 that alcohol was allowed to be sold in shops, hence the lack of options! The one store that does sell it is the Crackerjacks Whistletop market in Whistlestop mall. Definitely worth buying a bottle and drinking it while watching the sunset – especially if your accommodation has a deck!

image of pink and orange sunset from Bearskin Neck Motor lodge, Massachusetts

Total driving time: 1 hour 40 minutes

Where to stay: Bearskin Neck Motor Lodge

Where to eat: Blue Lobster 

Day 8 – Salem / Depart

For your final day on your one week New England Roadtrip, options depend on the time of your flight. If you have an evening flight, this is the perfect day to check out Salem. Famous for the witch trails back in 1692. However, Salem has a much richer history than just these trails.

An excellent way to discover more, is to take a trip on the Salem Trolley Tours. To find out more about this take a look at this blog post on the Salem Trolley tours!

image of red traditional Salem Trolley in Salem

If you still have some time before your flight, this is the moment to head to Target to pick up all the incredible bargains and homeware items to your hearts content!

Total driving time: 1 hour 15 minutes

Final thoughts on this One Week New England Roadtrip itinerary

When visiting New England you have to make some choices about which areas you want to focus your time and attention on, particularly if you are restricted on time. It is such a large area, it would be near enough impossible to cover everything in a one week New England itinerary. The danger with this would be to spend too much time driving to try and cover large distances and then not have enough time to actually get to know the places you are visiting.

This one week New England itinerary focuses on Vermont but gives a little taste of Maine and Massachusetts as well. Striking the right balance between distance and time.

Have you been to New England? What were your highlights? I’d love to know for where to go next time! 

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one week New England roadtrip image

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Brit Powless October 25, 2019 - 10:57 am

I love this region. Almost exactly 22 years ago, still in my 20’s, I took my then 15-yr old sister on a 10-day adventure. It was the first major trip I planned and scheduled all on my own. It was amazing and definitely anchored a love for travel for us both. We stayed in Lynn, suburb of Boston for a few days. Day tripped to Boston and Salem. Then drove to Mystic, CT for a few nights and day-tripped from there. Then stayed on the Cape for the remainder of the trip and saw as much of the island as we could. We whale-watched in Salem and Portsmouth, took haunted tours in Salem, saw the Amistad replica in Mystic and ate our weight in lobster rolls.

I’ve often thought about replicating that trip with all 3 of my sisters. Your post is fueling that fire! A wonderful piece.

Charlie - Where Charlie Wanders October 25, 2019 - 9:54 pm

Wow. I bet that was an amazing trip. And also giving me inspo for my next one! I will definitely be returning to this part of the world soon. I hope you make it back ASAP and I’m so pleased this post has inspired!

Latitude Adjustment: A Tale of Two Wanderers October 25, 2019 - 5:02 pm

Great post.

Charlie - Where Charlie Wanders October 25, 2019 - 9:54 pm

Thank you!

Kerry LifeandLoves October 31, 2019 - 9:04 am

Ahhhh Charlie I have been waiting to have proper time to get the lap top out and read this. I wanted to see the pics in full glory! I really want to visit this area of the US, and your trip sounds amazing. The photos alone have got me wanting to hop on the plane! Fab post and a great trip xx

Charlie - Where Charlie Wanders October 31, 2019 - 9:53 am

Oh Kerry!!! Thank you so much. This post did feel like a labour of love, and the trip was one of my favs in for ever. So this really means a lot! Xx

lakicabeatrice November 4, 2019 - 1:02 pm

Great post. The photos are epic. Cheers!!

Charlie - Where Charlie Wanders November 4, 2019 - 5:42 pm

Oh that’s so lovely! Thank you!

Courtney May 18, 2020 - 3:55 am

Omggg, this looks like such a cozy road trip! Definitely hope to do this someday. I still have so much to see in the north east! The clam shack just sounds so good too!

Charlie - Where Charlie Wanders May 23, 2020 - 12:47 pm

It was amazing!! Just felt so happy to be there!


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