(212) 564-1001 or (800) 999-8160

Most Popular Family Summer Vacations in New England in 2021

Most Popular Family Summer Vacations in New England in 2021

Growing up in Northeast Pennsylvania, the New England states were favored destinations by my parents for our summer vacations. In fact – I have frequented all of them – some more than once. Although very well known by those of us in the surrounding northeastern states – those of you in other parts of the country may not be as familiar with their allure. No worries. It’s my job today to familiarize you with them and hopefully, if I do my job well, you’ll be heading they’re on your family summer vacation this year!


Where is New England?

The area referred to as New England – or the New England states – are the northern most states located on the eastern side of the US. There are six of them and they include Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island and Vermont. It is interesting to note that this area is actually the oldest clearly defined region of the United States – and received its official moniker about 150 years prior to the American Revolution by one Captain John Smith of Jamestown, Virginia.

As for its origins? Well, you know that holiday we celebrate on the fourth Thursday of November as an ongoing tradition started by a group of people from England called pilgrims? How about a ship called the Mayflower? Ring a bell? Yup – that’s where the New England states got their start – that infamous 1620 voyage and subsequent establishment of Plymouth Colony. After which that corner– of what would someday be the United States of America – just took on a life of its own and grew from there.

Now – thanks to that colonial past – this is one destination – well technically six – that is the perfect place to sneak in a little learning – i.e. – travel as a living classroom. And what better way to learn than to be in the very place history was made? But it’s not just history. It’s also a pretty incredible area to head to if you love being in the great outdoors as there are plenty of beach destinations, state parks and other opportunities to get out and immerse yourself – and your family – in nature. And seriously – after being cooped up for the better part of a year – who doesn’t want to head outside this summer?

Now, obviously between six states and hundreds of miles there are plenty of cities, towns and regions to explore so let’s break it down into some manageable parts for you, under the categories of cities, beaches and parks.

Cities with Historic Charms

First up – that history I mentioned. Let’s go with the big three – Boston, Providence and New Haven – keeping in mind these certainly aren’t the only towns where history was made but are great places to visit and introduce the kids to where it all pretty much started.


Let’s see. The tea party. The infamous ride by Mr. Revere. The massacre. The baseball team winning their first World Series after an 86 year dry spell. (Oops. Sorry. That isn’t the type of history I was going to talk about. But man, that was some sports history right there.) In any case Boston is filled with history – starting with its colonization in 1630 by Puritan settlers – which makes it one of the oldest municipalities in the US. But Boston is not just historic – it is oh so charming as well. Even though it’s a “big city” – it never quite feels that way. Thanks to its cobblestone streets, brownstones, tours via trolleys, marketplace and colonial-era structures, it feels more like a small town atmosphere than a bustling urban center. Even the pace of the people who call it home is more reminiscent of a rural destination. And honestly – that’s what makes it so darn appealing. I love New York. I love Philadelphia. But I wouldn’t dare put them in the same “big city” category as Boston – which has a totally different city vibe – and a charismatic one at that.


Rhode Island may be the smallest of the US states – but there’s plenty to see and do and its capital city of Providence is a great place to start. Founded by Puritan Roger Williams – who was banished from Massachusetts due to “dangerous opinions” – it too can lay claim to being one of the US’s oldest cities. Throughout the delightful city of Providence, you’ll find turn-of-the-century buildings, one of the oldest zoos in the country, historic mansions and other architecturally fascinating residences, authentic Venetian gondola rides on the hard-to-pronounce (and spell!) Moshassuck and Woonasquatucket Rivers and of course, WaterFire. Now, since most of that list is pretty self-explanatory – let me tell you a little bit about the award-winning fire sculpture installation that is WaterFire. It can be found on both of those hard-to-pronounce rivers mentioned above – as well as on a third river that passes through the city – aptly named Providence River. Consisting of more than 80 bonfires blazing above the surface of the water and running for about two thirds of a mile – WaterFire is visible from various locations around the very walkable and beautifully revitalized riverfront areas and is a must see during your visit.

New Haven

On to Connecticut and the city that a little university named Yale calls home – New Haven. Like its predecessors above, it too was founded by English Puritans in the 1630’s. It’s claim to fame is that it was one of the first “planned cities” in America that eventually grew to be an important industrial center back in the day.  In fact, some pretty well known inventors and industrialists called New Haven home including Eli Whitney (the cotton gin), Charles Goodyear (yes – vulcanized rubber and where that tire company took its name from) and Oliver Winchester (manufacturer of repeating long arms and ammunition). The lovely city of New Haven is also home to several sandy beaches, many historical sites – with 59 of its properties listed on the National Register of Historic Places, plenty of arts and entertainment, several museums, what some claim to be the best pizza in the country, Lower Dixwell – site of the largest African-American parade in New England called the “Freddie Fixer” Parade and fabulous markets like Wooster Square Market that brings vendors from all over Connecticut to town – just to name a few.

Sought-After Summer Beach Resorts

Next – let’s check out some of the most popular – and beautiful – shore points that can be found in New England – because what kid doesn’t like to make sandcastles, jump waves and bury their dad up to his neck in sand?

Martha’s Vineyard

I first visited Martha’s Vineyard when I ten years old on yes – a family summer vacation and besides the prettiest, most colorful little houses I had ever seen in my then short life the one thing I remember vividly was that there was a film crew on one of the beaches we passed by while on a tour bus. Turns out they were filming a little movie about a great white shark terrorizing a New England Beach town that maybe you have heard of? Queue the Jaws music! Accessible only by ferry – or air – this idyllic island off the southern coast of Massachusetts is filled with fun family activities. Check out it’s lighthouses – five! – rent bikes and explore the isle via two wheels, take a spin on the oldest continuously operating carousel in the nation – the Flying Horses Carousel, take in some incredibly cute alpacas at the Alpaca Farm, visit the “Jaws” bridge – where all you children of the 70’s better make me proud and take a jump off of – yes you’re allowed! – and of course hit one (or more) of those scenic beaches. All this – as well as one of the most dramatic and beautiful cliffs you’ll ever see – the Aquinnah Cliffs –await you on the oh so enchanting Martha’s Vineyard.


Many people who visit Massachusetts get stumped when deciding whether to do a day trip to The Vineyard (as it is referred to in these parts) or to Nantucket. And I say – either way you will NOT be disappointed. Nantucket – also off the southern coast of Massachusetts, is the smaller of the two islands – but no less charming. While there are six towns that make up Martha’s Vineyard, Nantucket has just one. Here the houses – though not as colorful – are still unique in that the majority bear the unpainted cedar shingle look of the past. Family activities to partake in on the isle? Well, it’s history as a major whaling port in the 19th century means a visit to the Whaling Museum is a must. Three more lighthouses to climb. Plenty of beaches – including Children’s Beach which – you guessed it – is a child friendly beach – and park. A nature walk through the Coskata-Coatue Wildlife Refuge for a peek at some rare but friendly creatures. A bike ride along the scenic Sconset Bluff Walk that takes you through quaint neighborhoods filled with colorful blooms. And let’s not forget about the adults. For the family matriarchs and / or patriarchs there’s Cisco Brewers for craft beer and music and of course there’s plenty of shopping, golf and spas for that oh so important wellness aspect! – to be found here too.

Cape Cod

If you prefer not to leave dry land, you’ll find that the hook-shaped peninsula called Cape Cod is just as charming as it’s islands to the south. Access to forty miles of seashore puts it on the list as one of New England’s best beach destinations – so a day at the beach – check! But there’s more. First, there’s the Sandwich Glass Museum where you can not only view historical and modern glass art – but you can also see the glass blowing process up close and personal. (Bonus – kiddos age five and under get in free.) Then check out the Heritage Museum and Gardens for one hundred acres of serene surroundings – as well as an antique car exhibit for you car lovers and a children’s area with plenty of fun activities to keep their attention for hours. Head to the tip of the cape where in Provincetown you’ll spy The Pilgrim Monument – which at 252 feet tall is the tallest all-granite structure in the United States and is well worth visiting, and climbing, for a breathtaking view of your surroundings. Here you will also a museum which highlights the arrival of the pilgrims among other historical events of the area – which allows you to sneak in a little history lesson. And speaking of history – my dear mother was enthralled with the Kennedy family which meant a trip to Cape Cod also meant visiting the JFK Memorial and the John F. Kennedy Hyannis Museum. So obviously I cannot talk about the Cape and not mention these two attractions – both in Hyannis – especially for my Kennedy family enthusiasts out there. You’re welcome mom.


And now let’s depart Massachusetts and take a look at our next pick for a great New England beach destination. We’re heading back to Rhode Island but this time it’s to the city of Newport, which is also an island destination, as it sits on the end of Aquidneck Island. It may not be as popular or even as well-known as the first three picks – but has just as much appeal and plenty of things to do for the whole family. To start – since we are sending you here for the ocean you absolutely must do the Cliff Walk while in town. At three and a half miles the views are spectacular – not only of the eastern shores but of the luxurious villas you’ll spot dotting the cliffs. If you prefer not to walk (and not end up having to carry that tired three year old) then do the Ocean Drive instead. Filled with just as spectacular shoreline views as the Cliff Walk – as well as a number of landmarks – it has earned a designation as a National Historic Landmark District. During your drive be sure and keep your eyes open for opulent mansions, a US Coast Guard station, the Hammersmith Farm where President Kennedy had his wedding reception (hear that mom?) and more. Finally, be sure to visit mile and a half long Thames Street for shopping, dining, bars, museums and historic homes, as well as access to several marinas and the Newport Harbor – which are home to some pretty lavish yachts.

National Parks And State Parks

And last, but certainly not least, let’s take a look at everyone’s favorite mother – good old Mother Nature and just three of the many parks that you can find and explore in this very scenic part of the good old USA.

Acadia National Park

You may be surprised to learn that out of the six New England states there is only one national park – Acadia National Park – and it calls the northern most New England state of Maine its home. Acadia also happens to have several notable and impressive distinctions. It’s the first national park decreed on this side of the country, it’s one of the top ten most-visited national parks in the US and it boasts the highest point along the North Atlantic seaboard – Cadillac Mountain. Fun Fact: At just above 1500 feet, Cadillac Mountain is the first place in the United States to see the sun rise! It also offers fabulous views of Bar Harbor – which is a small but oh so quaint coastal town probably best known for its lobsters. And I feel I must add another childhood antidote here – humor me – as when I visited Bar Harbor as a child, my parents bought me what would be one of my most prized childhood possessions – a vinyl autograph lobster (yes, vinyl autograph animals were “a thing” in the 70‘s).

Mount Washington State Park

Ever hear of Sargent’s Purchase, New Hampshire? Me neither – until I researched state parks for this blog you’re reading. It’s where you will find Mount Washington, and its namesake state park, whose claim to fame is the view from the Northeastern United States highest peak. At its 6,288-foot summit, high above White Mountain National Forest, views go far beyond New Hampshire – like 130 miles beyond – to Vermont, New York, Massachusetts, Maine, Quebec and the Atlantic Ocean! And while visiting be sure and check out the oldest surviving building on the summit – the Tip-Top House.  Made of rock blasted from the mountain it is also believed to be the world’s oldest mountain top inn. You can also find the Mount Washington Observatory here – which is a weather research station. Apparently, whoever decided to place the observatory here made a good call as the summit is known for having some of the world’s worst weather! Yup – and that apparently includes an once world-record wind speed of 231 miles an hour – which was held until 2010. Another Fun Fact: Among the many trails you will find running up and around Mount Washington is the hugely popular 2,180 plus mile long Appalachian Trail!

Boston Harbor Islands State Park

And now going back to where we first started – Beantown. Located mere minutes from downtown Boston, Boston Harbor Islands State Park consists of 34 islands and peninsulas – with scheduled ferry access to two of them – Spectacle Island and Georges Island. Now if you are a history buff, I suggest hopping the ferry to Georges Island where you can explore Fort Warren – which is a civil war era fort that took so long to build it was pretty much obsolete by the time it was completed. However, the island did assist in the war efforts as a facility for the Union Soldiers to train – securing a place in history. Should you opt to head to 114-acre Spectacle Island bring your hiking shoes and your bathing suit as both are viable options here. If you decide to hoof it around the island, be sure to take in the fabulous views from the top of North Drumlin – the tallest point in Boston at 155 feet above sea level. If you prefer to relax by the sea instead – there’s an accessible lifeguarded beach here for all to enjoy on those warm northeastern summer days.


And that, my friends, is New England in 2500 – give or take – words or less. How’d I do? Ready to visit for your family summer vacation this year? You do know that your friends at Beyond Times Square can help with accommodations, transportation, tours and more throughout the New England states, right? Well, you do now! So why not give them a call and let them do what they do best – help you plan a luxury trip to New England that you and your family will be reminiscing about for years to come!