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An epic New England holiday – see all 6 states in 15 days

Known for its fall colours and miles of coastline it can draw crowds, popular with visitors from all round the world, eager to fill their New England holiday with the burnt oranges, deep reds and sunshine yellows of the autumn leaves. Or to spot the hundreds of lighthouses that dot the coastline and make picture postcard photos.

November 27, 2022


Why New England

When I was researching our New England holiday, most forums said it wasn’t an easy trip to do, that sounded like a challenge to me and if I’m honest when visiting an area, I like to see as much as possible, often to my husband’s dismay.

New England is an area in North West America comprising six states; Maine, New Hampshire, Vermont, Massachusetts, Rhode Island, and Connecticut. Each state is relatively small so it isn’t quite as an imposing mission as you might think.

Known for its fall colours and miles of coastline it can draw crowds, popular with visitors from all round the world, eager to fill their New England holiday with the burnt oranges, deep reds and sunshine yellows of the autumn leaves. Or to spot the hundreds of lighthouses that dot the coastline and make picture postcard photos.

Discovered by the English in 1620, it soon became a place to settle, hence the many place names mirroring ours here in the UK, often confusing with 3 Manchester’s in 3 different states! Tip no 1 make sure when planning your New England holiday, you know exactly which one you are heading to.

New England has a chequered history, after the first English colony settled in Plymouth much followed, becoming the centre of the anti-slavery movement and industrial revolution, the centre of manufacturing for the whole United States and playing an important role in the American Civil war.

Today however it is a huge tourist area due to its rich history and beautiful scenery and coastline.

For our New England holiday, we chose to come in what is described as shoulder season, the time bridging the gap between high season (summer) and low season (winter).

This meant we avoided the thronging crowds of summer and the masses arriving to see the fall colours in their peak. From my research, this can bring roads to a standstill, and the trails and beauty spots in Vermont especially, to a crawling snail’s pace.

My itinerary forms a loop to drive through each state, starting and ending in Boston. Taking in the major must see’s and destinations, if you want a lazy trip with days and days in each place, then you could break this down into several trips but as we are relatively young and or stupid, we decided to just go for it and do what we could, this resulted in a fair bit of driving and pretty full days but it was worth it.

We have seen enough to know where we would return to and discover more, or to have ticked off our travel list as job done.

Each state has enough to make it an independent New England holiday destination, but for us as a couple we have such a huge bucket list that we wanted to see and do as much as we could in the time we had, so there will be things that we missed or could have spent longer in and I will try to include those in my account.

Arriving into the USA to start your New England Holiday

Boston is the most popular airport to fly into, and if from the UK the ideal place to kick off your New England holiday, alternatively you could fly into New York and travel in from there, this was our original pre covid plan, but this changed after 2 years of setbacks.

There are also many other smaller airports if you are flying in from other states as well as a pretty decent rail service and buses travelling between them. You can also catch a ferry fro Boston to Cape Cod.

We arrived late evening into Boston airport, picked up our hire car which was an easy hop on complimentary bus ride away and made our way to our first night hotel just a short drive from the airport. By the time we checked in it was around 11pm USA time and for our poor sleep deprived body clocks 4am!

We stayed at a Comfort Inn, it was cheap and cheerful and unexpectedly, provided one of the best breakfasts we had on our trip, it was just a place to rest our heads after a long and tiring days ravel.

We were up pretty early and set off to our first destination on our New England holiday road trip, Cape Cod. In hindsight exploring Boston first might have been more sensible, as even though it is a small city and easily covered a lot on foot in a few days by the end of our 15 days we were a little tired, more of that later.

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Cape Cod – Massachusetts - Days 1-3

As we were up bright and early it was a fairy easy drive out of Boston, the roads were quiet and our drive to our first stop the coastal town of Plymouth took less than an hour.

Site of the first Pilgrim settlement, the town was an attractive introduction into the Massachusetts area, Plymouth Rock, a boulder in Pilgrim Memorial State Park, and marks the place where settlers are thought to have landed on shore.

The Mayflower II, a full-scale replica of the ship that carried the Pilgrims across the Atlantic, is found here. We took a leisurely stroll around the small town, and enjoyed the quintessential New England feel and historic architecture, that Plymouth offers.

Places to see –

Plymouth farmers market, held every Thursday from May to October and once a month during the winter you can be sure to find the best local produce.

Plymouth Rock as mentioned above, note - there is a charge for stepping on board the Mayflower 11, we chose to just view it from the outside.

The museum and other historic buildings.

You can also grab a clam chowder in one of the many eateries in the town and seafront.

It was by now late morning, and we continued on to stop at Sandwich, Dennis and Yarmouth, each worth a short visit.

See the heritage museum and gardens in Sandwich, spot your first lighthouse at Sandy Neck beach, or ride a bike along The Shining Sea Bikeway, a rather unique trail that goes through a few towns in Cape Cod, but mainly through Falmouth. The trail can be reached by a short drive from Sandwich.

We walked the Sandwich boardwalk, constructed in the 19th century and renovated many times due to the coastal weather conditions. It has great views and worth a visit.

West Dennis has some quirky trinket shops, surfy boardy type clothing stores and souvenir shops, along with some buildings with stunning architecture. East Dennis has a marina with some luxury boats moored there, we only had a short break here before arriving in our charming destination of Chatham for our 3-night stay.

We chose to stay in a traditional Inn, very popular for a New England holiday and especially in this part of America. The Chatham Gables Inn is hosted by Nigel and Amanda who provide a wonderful bed and breakfast experience, in their historic New England Inn. Built in 1839 as a sea captain's home, the house has lots of New England charm and modern elegant decor to bring it up to date.

We especially loved the home-cooked breakfast, each night a beautifully designed menu is posted under your door and you have 2 options to choose from. During our stay we had a steak and egg muffin, blueberry pancakes and a BLT sandwich. This is a leisurely affair so if you have a full agenda ahead make sure to get down to breakfast first.

Outside, the gardens are full of softly faded hydrangeas, covering the Inn and veranda offering a tranquil spot to relax on a warm summer evening, even in mid September we found the weather mild and sunny.

Upmarket Chatham is a seaside town with exclusive shops, galleries and eateries, situated on the elbow of the Cape. Famous for its beaches and the Chatham lighthouse.

We found it a very good location to explore The Cape. A highlight of our stay was watching the sun rise on the nearby beach, and seeing the seals swim past us in the sea and dipping and diving for attention at the Chatham fishing pier.

This was an expensive choice of accommodation and there are many other lower cost hotels and Inns nearby, Chatham however is upscale and is more costly than other areas on the Cape. As we drove around we were very envious of some of the beautiful mansion style houses we passed in the area. Randomly, quite a few have wild turkeys just wandering around outside of their properties.

You can see why Cape Cod is a popular New England holiday destination, as it can easily capture your heart, with its wildlife, lighthouses and beautiful 40 miles of dramatic National seashores. People come back time and time again. Many Americans have holiday homes here, but that does mean it is chocca in the summer, however, when we visited these houses were empty which we thought to be a shame.

We explored the National seashore stopping at beautiful beaches such as; Coast Guard Beach, Truro, and the lighthouses of Eastham and Highland links, before reaching the vibrant, funky and anything goes Provincetown, also known as PTown. Right at the end of the Cape Cod peninsular, it is a must on your New England holiday road trip. Provincetown is famously known as having one of the largest LGBTQ+ communities in the country and is a haven for artists, which is evident with the many galleries, arty shops and riot of colour everywhere you look

We wandered around the lively multi-coloured town, before catching a pre-booked whale watch boat trip with Dolphin Fleet. It was superb, a truly memorable thing to do. The time out on the water was around 3-4 hours, and we were so lucky to see a pod of around 30-40 Humpback and Minke whales, the absolute highlight of our New England holiday.

No stay on the Cape would be complete without a drive-in movie at the Wellfleet drive in cinema. The showing was of course Jaws, synonymous with Cape Cod, stop by the infamous Jaws Bridge in Martha’s Vineyard if you take a trip there.

We spent a day in Nantucket, boarding the Hyline ferry from Hyannis which was an hours ride away.

Arriving in Nantucket you are met with charming little shops and cobbled streets, wharfs filled with cafes, restaurants and churches. If you love lobster rolls and oysters you will find them in abundance here.

The whaling museum tells the history of the islands role as a whaling hub.

We loved Nantucket, it is only a tiny island but it is the epitome of picturesque, you can explore a lot on foot, hiring a bike would be ideal, but as we only had a day, we caught an Uber to the other end of the island to stroll the Sconset Bluff walk, a delightful cliff top path, partly made of sparkly white sea shells that takes you right through the gardens of the magnificent cliff top homes that wouldn’t look amiss on a movie set. Again, these seemed mostly empty and you couldn't help but wonder who lived in houses like these!

This spectacular path winds all the way down to Sankaty lighthouse with views down to Sconset beach, we happened upon a collection of painted shells, turn them over for a surprise joke.

Before departing we walked down to Brant Point Lighthouse, one of my personal favourites. We could have spent another day here to really do the island justice and wouldn’t hesitate to return.

As if one island wasn’t enough, the next day we departed Chatham and caught another ferry from Woods Hole to Oaks Bluff, Martha’s vineyard. A car ferry this time as MV is a much larger island, and summer bolt hole of the rich and famous and known to most as the setting for the 1975 film Jaws.

You could easily spend a few days here to take In the remarkable beaches, New England architecture and variety of wildlife parks and refuges.

A must see are the gingerbread houses of Oaks Bluff, an assortment of pastel painted houses straight out of a children’s fairy-tale, with balconies and intricate wooden trims, porches made for sitting on, in every muted shade from baby pink, mossy green, primrose yellow and cornflower blue.

The history of these homes starts in 1835, when some local Methodists began holding religious camp meetings on some land they bought in Oaks Bluff according to the Martha Vineyard’s Campground Association, who maintains the houses today. By 1855 there were over 200 tents pitched on the site, which became unsuitable for family vacations so the cottages were built to replicate the original tents.

They are a breath-taking sight and you will wander round in wonder that such a place even exists, aside from in a children’s story book. A photographers and artists dream; you won’t be disappointed by your visit here and it is free to enter although the museum on site charges and entrance fee.

We bought a bus ticket and used this to get around the various other sites we explored during our visit to Martha’s Vineyard, the island gets its name from a British explorer who landed at Cape Cod and named this island after his daughter.

We rode the oldest carousel in the USA, flying horses also in Oaks Bluff, we explored Edgartown, once a major whaling port, now an upmarket town with its streets lined with boutique clothing stores, cafes, bakeries and galleries.

We happened upon a gorgeous and boujee café named behind the bookstore, because yes, it is indeed tucked away behind the local bookstore. We sat under a canopy of trees and shared some lunch. Everything here is quite highly priced, an average sandwich and drink will set you back around £20p.p at time of writing.

After finding some more Jaws locations we headed back to the mainland to continue to our next state and next leg of our New England holiday.

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Newport – Rhode Island – Days 4-5

The Bayberry Inn was our home from home during the two night stay we had in Newport, the second state on our New England holiday. A boutique luxury Inn situated in an ideal location in the heart of historic hill.

This was our favourite stay and location during this New England holiday, an ideal mix of coastal culture and townie convenience.

There is a lot to see and do here, we liked the chilled but modern vibe the area offers.

The Bayberry is another traditional Inn built in 1837, and the former home of a Navy Captain, it has traditional character but has been cleverly modernised to be stylish and contemporary. We had a The Anna Hunter suite with a Jacuzzi bath and fire if we had needed it and it was absolutely gorgeous. I cannot find any fault with our stay here.

Breakfast was included and the chef provided a lovely selection each morning, it was a more casual affair that suited us better, served in the elegant dining room it was a lovely way to start our day.

Though Newport is a small town, it boasts a large amount of attractions and places to visit, from the International Tennis Hall of Fame, Newport Art Museum, the wharfs along the marina, the shops and restaurants and beaches.

Newport is also where you’ll find the Gilded Age Mansions on Bellevue Avenue, The Breakers being the grandest and former home of The Vanderbilts, one of Americas richest families, a summer get away for the socialites.

There are 7 mansions to visit in total with the largest and finest being in the same area, making it very easy to visit. Insider tip – we found it most cost effective to buy an annual membership that gave us access to everything including free parking at all sites.

We did however only visit the mansions that appealed to us the most. We also visited the Green Animal Topiary Garden, just out of town it features over 80 topiary animals and birds and the most stunning collection of dahlias and was a pleasant way to spend a few hours.

Another highlight of the area is the Cliff Walk, on the Eastern shore, the walk takes in the natural beauty of the Newport coastline and the architectural history of the Gilded Age. These mansions are a bit like the UK’s stately homes but imagine that they have been sprinkled with gold dust and bling and you might come close to the opulence that they exude.

The walk is 3.5 miles long, with three quarters of it being an easy walk, the last part is uneven and comes with safety warnings, so if you aren’t sure footed you can easily leave before this point.

Newport town is packed with bustling wharfs, cobblestone streets, shops full of souvenirs, home décor and places to eat. During our New England holiday stay in Newport we found the Brick Alley Pub which has been voted both "Best Restaurant" and "Best Bar" in Rhode Island. We loved it so much we chose to eat there both nights of our stay.

It is clearly a popular place as the tables and bar were full and with over 25 beers on tap and a huge menu to choose from, combined with funky décor and a cool atmosphere it comes as no surprise. The walls and ceilings are full of signs, posters, car parts and various other quirky paraphernalia, making the vibe trendy and fun. We probably would have eaten here every night if we’d been staying longer as the food was a real highlight.

Newport is most definitely on our revisit list, most likely combined with a trip to New York as a multi-centre New England holiday, we’d like to explore this versatile town and coastline even further.

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Manchester & Woodstock Vermont – Days 6-7

Day 6 saw the longest leg of our driving time, in total it is about a 5-hour drive between destinations, what you’ll notice is that the distance seems shorter than the drive time, this is down to the strict speed limits in the area, and in some places the type of country roads you are travelling on. We did find driving relatively easy though and everything is signposted clearly.

A GPS is a worthwhile addition to your car hire to make navigating your New England holiday easier.

We broke up the journey with several stops, firstly Mystic Seaport made famous by the Mystic Pizza movie, we thought The Mystic Seaport Maritime Museum looked worth a visit, but it was drizzly when we were there so we didn’t stop long.

By the time we reached Stockbridge & Lenox both lovely quaint small towns to see we were pleased that the sun was shining again, warning - there are two towns named Woodstock so get your coordinates right!

Our first night in Vermont was spent at the Equinox Hotel & Spa lying at the foot of Taconic Mountains, it is a nice hotel in the green mountains, but probably not worth the money we spent for just 1 night there. Manchester is posh, Hildene, the estate of Abraham Lincoln’s son Robert is the main attraction and even the pavements are made of marble.

It is a shopper’s paradise with outlets and small shops lining the streets and the area is a ski resort in the winter months. We noticed the temperature dropped dramatically here.

We attempted to drive the Mount Equinox Skyline drive, the longest privately owned paved toll road in the U.S. Described as an unforgettable scenic drive to the summit of the highest peak in the Taconic Range. Sadly, for us the weather did not play fair and it was too overcast and cloudy to see anything, so we had to move on to our next stop of Woodstock.

Woodstock - Vermont

A picture postcard town in Vermont, Woodstock is a town not to be missed on your New England Holiday tour. There is a lot to see here including a traditional covered bridge, Billings Farm & Museum a functioning dairy farm with an 1890’s farmhouse that creates 19th century farm life.

The surrounding area is a photographers dream, with a few farms being some of the most photographed and posted on Instagram.

These farms take some finding and are tucked out of the way in rolling countryside and colour changing tree’s. Sleepy Hollow Farm and Jenne Farm are the most popular, be prepared to drive about 15 minutes outside of Woodstock and take your chances on the bumpy farm tracks.

We stayed in another traditional boarding’s - The Jackson House Inn, built in 1890 is as historic as they come, from the squeaky wooden floorboards to the classic bedroom styling, you are getting to sample a piece of New England living.

Breakfast was again included and is uniquely inspired by sourcing only the freshest local ingredients, you do not get a choice however so this might not suit some people.

We enjoyed our time here although in hindsight we may have just stopped for a visit and not stayed the night. It was a convenient place midway between destinations though.

Kancamagus Scenic Byway to Lake Winnipesaukee  – New Hampshire - Days 8-9

We drove the hour and a half journey to Lincoln to start the stunning “Kanc” as its lovingly known locally, It covers a 34.5 mile scenic drive in Northern New Hampshire, ending in Conway and is well known as one of the best Fall Foliage viewing areas in the world, it winds its way through the majestic White Mountains with many sights to stop explore and hike.

I can only imagine how jaw dropping this area is in full Fall colour, as we drove through, the colours were just changing mostly bright yellows and coppers, with the odd tease of a burst of the deep red that was to come.

There are many vistas, scenic photo stops, waterfalls, covered bridges and viewpoints to see as you take in the natural beauty that is all around you.

In full season, which is around for only a few weeks and varies according to the years weather, the area draws in millions of visitors, so whilst we didn’t get to see it in all its glory we also didn’t have to deal with the crowds and traffic jams. Parking was pretty packed even during our visit so It must be chaos at full capacity.

After exiting at Conway we drove down to the lakes area of Winnipesaukee and Winnisquam ,or as you might know it “On Golden Pond” located at the foothills of the White Mountains it gives a pleasant break from the driving and there is something calming about lakes with the mesmerising reflections, especially at this time of year.

As with any lakeside vacation spot, there is an abundance of things to do, fishing, boat trips, nature spotting or just chilling listening to the water lapping on the lake shore. It is a year round resort with the skiing and snowboarding in the nearby mountains.

We could have spent several days here if we had had time to visit the nature reserves and take a boat trip.

Portland and Maine Coast – Maine – Days 10-11

City life beckoned, and we arrived in Portland, a fairly compact city, set on a peninsula spreading out into Casco Bay. The Old Port waterfront features working fishing wharves and converted warehouses with mostly seafood restaurants and enticing shops. You need to like seafood here, especially lobster rolls and clam chowder. There are other choices but it is predominantly seafood. There is also a big beer culture here, and the locals describe themselves as real foodies.

Nearby, the Western Promenade is a public park right on top of a bluff, with awesome river and mountain views, we spotted chipmunks darting in and around the trees, and hiding under surf boards stacked up at the beach.

Its surrounding district, the West End, is full of Victorian-era homes, including the Victoria Mansion museum.

This seaside city has a big history including many fires in which large parts of it were destroyed and rebuilt. We toured the area in a converted and restored traditional fire engine, this was a fun way to get the history and get our bearings and the conductor gave us a humour filled narration as we drove around.

Whale watch tours depart from the docks and you can visit nearby islands within Casco Bay. We found a full day and two evenings here enough to see what we wanted to.

Plum Island – Massachusetts – Days 11-12

You can’t miss the many coastal towns and villages and of course lighthouses that line the Maine coast and into Massachusetts.

We stopped to see; Cape Elizabeth, Fort Williams Park, Kennebunkport which we loved, a quirky small coastal town, a nice place to stop for a coffee, with beautiful beaches.

then on to Ogunquit, we would have loved to have spent more time here, and would have spent a night here instead of two in Portland if we had known how lovely it is. Of course, there is a also a lighthouse to explore. The surrounding neighbourhood is upmarket with stunning houses with a beachy feel, and lovely cafes and shops. The type of cafes we had missed until this part of our New England Holiday. We enjoyed some freshly made sandwiches sat outside a cafe in the sun.

Plum Island is a little slice of paradise, we were in need of a bit of R&R before our final destination of Boston, and we were stunned by the beauty of the beach that was literally on our doorstep at the Blue Inn On the Beach, our home for two nights.

We especially loved this accommodation as our mini apartment opened onto a large deck with a hot tub with steps straight onto the beautiful sandy beach. In fact, we could lie in bed with the view of the ocean through our doors, we went to sleep and woke to the sound of the waves lapping the shire, Idyllic.

This really was the perfect New England holiday haven. Just a ten minute drive from the lively town of Newburyport full of shops and restaurants and just an hour’s drive from Boston.

The Parker River National Wildlife Refuge originating in 1942 takes up the southern two thirds of Plum Island, It is a stopover for over 300 species of migratory birds, providing them the ideal habitat to flourish. You can swim, hike, surf and birdwatch here.

We would highly recommend staying at the Blue Inn on the Beach, it is off the beaten track and a welcome break to relax and chill before returning to the hustle and bustle of city life and the most relaxing of our stays. Each morning we were left a picnic basket with freshly made egg salad and baked goods with a hot flask of coffee to enjoy. The communication and friendliness of the staff here was excellent.

The last leg of our New England holiday was to return to Boston for our final 3 days, on the way we stopped at the delightful fishing town of Rockport, right at the tip of the Cape Ann peninsular and showcasing picture perfect scenery.

We strolled around Manchester by the sea, watched the waves gently lapping onto Singing Beach before having lunch in Salem, a historic coastal town famous for its 1692 witch trials. The House of Seven Gables is a popular tourist spot to visit, built by a wealthy merchant in 1668 it has become one of Americas most loved historic homes.

The Salem Witch trials, an extraordinary event that made this illustrious town what it is, hanged 19 innocent people as the courts believed in the devil at that time, but thankfully these trials were abandoned at a later date and those awaiting execution were pardoned.

In today’s Salem, modern day witches still reside here through the community’s emphasis on the importance of human rights and acceptance. The town is full of witchy merchandise and we saw many people dressed up, although I’m not sure if this was on account of their visit or their usual attire.

Salem is the base for many movies and TV shows such as Hocus Pocus.

We then dropped our car back at the car hire company, and got an Uber to our hotel in the theatre district and near to Chinatown for our final few days of exploring on our New England holiday.

To read out about our time in Boston please check out my 48 hours in Boston guide coming soon.

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Top Tips

1. Get a Sat Nav/GPS - it makes driving really easy
2. Know your destination, New England has so many duplicate towns, you could find yourself in the wrong state!
3. If travelling in shoulder season be prepared for some places to be closed or have limited hours.
4. For good restaurants - book ahead. Some needed 3-4 weeks notice.
5. If you don't like seafood, finding other options can be tricky in some places.
6. Stock up of drinks and snacks as some of the routes do not have eateries en route.
7. Plan parking, especially if in busier seasons.
8. Try Uber, it is awesome for getting around in cities and islands.
9. Look at annual memberships for visitor attractions, some are cheaper this way.
10.Take a variety of clothes, the weather can be changeable.

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November 27, 2022