New England has always been on my bucket list. Growing up in the early 2000s, watching films like Hocus Pocus and Practical Magic, I have always been intrigued by this wooded wonderland and its tales of witches and legends of revolution. When I finally had the opportunity to visit earlier this year, I was eager to fit in as much as I could.
Starting in Boston, I embarked on a journey through all five states, travelling coastlines and mountains, enjoying the very best of New England. From lobster rolls to ice cream graveyards(!), there is a lot to enjoy here.
One of Freedom Destinations’ most popular New England itineraries is the New England Explorer, a fly-drive holiday that takes you through some of the area’s highlights over four states.
Here’s what experiencing it is really like…
The journey begins in Boston, Massachusetts. Founded in 1630, Boston was an important city both before and after the founding of the United States. The path to Revolution started here, with an event that you can recreate yourself at Boston Tea Party Ships and Museum by throwing your own chest of tea from a boat.
Fuelled with the fire of rebellion, you can grab a guidebook and embark on the Freedom Trail, stopping off at key revolutionary sights. From the tiny grave of Paul Revere, in Granary Burying Ground, to the site of the Boston Massacre and the obelisk of the Bunker Hill memorial, this walkable trail is an ideal way to explore the city. A handy, red-lined route on the pavement guides you throughout the 2.5-mile route, making it (almost) impossible to get lost.
Another renowned Boston attraction is the Duck Tour, which involves boarding an amphibious vehicle captained by a Bostonian skipper, who will talk you through the city (with some personal anecdotes thrown in) as you drive the streets, before plunging into the Charles River for a mini cruise. Boston is also home to the ‘Cheers’ Bar – a must-visit for any sitcom fan.
Lobster rolls and Clam Chowder are two of Boston’s most traditional dishes, best sampled at a food hall like Quincy Market or Boston Public Market. Seafood is an important part of the cuisine across coastal New England, and throughout this trip you are guaranteed to come across a delectable variety of it.
Taking to the road, you’re heading north to Southern Maine. As you drive, you’ll notice that Salem is on the way, which is well worth a stop. The infamous home of the Witch Trials in 1692, Salem offers a unique selection of attractions including the Salem Witch Museum and the Peabody Essex Museum. Don’t forget to snap a selfie with Samantha from Bewitched and pop into Black Craft Coffee for refreshments.
Arriving in Kennebunkport, you will immediately be surrounded by the charm of a New England coastal town. Once a major shipbuilding hub, in modern times the town has become a relaxing place to holiday, for both tourists and well-known public figures. The summer home of President H.W. Bush can be found on a nearby peninsula, and while not open to the public, it is possible to view it from the Walker’s Point scenic overlook.
At the centre of town is Dock Square, where you’ll find a variety of galleries and shops housed within 18th-century buildings. Many shops, like Copper Candle, feature locally made goods and an eclectic array of merchandise to browse. You can also jump on a 60-minute town trolley tour from here, which will take you back through 300 years of local history.
Down on Arundel beach is Spouting Rock, best seen on a windy day when the tide is high. As the waves crash upon the rocks, it sends a jet of water upwards; a dramatic spectacle on this rugged coastline. Further along the coast is Blowing Cave Park, which offers similarly breathtaking views.
Travelling further into Maine you’ll head inland before looping back to the coast and reaching Bar Harbor on Mount Desert Island. Considered one of Maine’s most picturesque destinations, the views here are nothing short of spectacular. Bar Harbor is best known as the gateway to Acadia National Park, but there is a lot more to love about this coastal town.
Walking the sandbar to Bar Island is a fun way to start your time here, crossing just before low tide and taking the short trail on the island for panoramic views of the harbour. There is only a 3-hour window for crossing, however, so plan carefully to avoid being marooned until the next low tide.
The Bar Harbor Shore Path offers views of Frenchman Bay, the Porcupine Islands, Egg Rock Lighthouse, and the Schoodic Peninsula. On your way you’ll pass Balance Rock, a large and precarious looking boulder, left behind on the shoreline by a melting glacier 10,000 years ago.
Bar Harbor Whale Watch Co. operates Maine’s largest whale watching fleet, and during whale season (late May to October) it’s possible to see humpback, finback and minke whales, plus dolphins, seals, and sometimes even ocean sunfish.
Today you’ll head into the National Park which surrounds you on Mount Desert Island. Acadia National Park is especially beautiful during autumn, but with winter skiing and summer hiking, you are sure to enjoy your visit whatever the season.
Starting at Hulls Cove Visitor Centre, collect a map and park pass before making your way out to explore. The Park Loop Road is a good place to start, a 27-mile scenic drive around the east side of Mount Desert Island with plenty of opportunities to jump out for a hike and sightsee.
For those interested in a more challenging hike, the Beehive loop is one of the park’s best-known rung and ladder trails. Featuring steep granite staircases and exposed cliff faces, this 1.4 mile trail should only be attempted in dry weather by experienced hikers. There are over 150 miles of trails to choose from, and family-friendly options like the Jordan Pond Path are also available.
New England holidays by Freedom Destinations
Boston | Kennebunkport | North Conway | Stowe | Mystic | Cape Cod
Boston | New York
Boston | Plymouth | Cape Cod | Hyannis | Newport | Providence | Killington | Stowe | North Conway | Portsmouth
Boston | Kennebunkport | North Conway | Stowe | Mystic | Cape Cod
Boston | New York
Boston | Plymouth | Cape Cod | Hyannis | Newport | Providence | Killington | Stowe | North Conway | Portsmouth
This morning you’re back on the picturesque roads of New England, crossing from Maine into New Hampshire to visit the White Mountain National Forest. This 800,000-acre area is home to Mount Washington and the Kancamagus Highway; considered one of the region’s best scenic drives for fall foliage.
Franconia Notch State Park is located within the Forest, with its own passenger cable car to transport visitors to the top of Cannon Mountain for some breathtaking views. On a clear day you can make out the distant peaks in Vermont, Maine, New York, and even Canada!
Mount Washington is known for having some of the self-proclaimed “World’s Worst Weather”, due to its location at the intersection of major storm tracks. Despite hurricane force winds (75mph) occurring more than 100 days per year, the peak is home to a cog railway, that bravely travels up one of the world’s steepest track lines. Riding the Railway has been a tradition for tourists for over a century, and the summit features an observatory, museum and visitor centre.
If a scenic drive or ride up a mountain isn’t for you, there are plenty of hiking trails to follow further down. The Tuckerman Ravine trail is a favourite among hikers for its glacial headwall views, although it can be strenuous. For summer hiking the Ammonoosuc Ravine Trail is a scenic, wet route on the west side, passing waterfalls on the way.
You’re crossing over a state line once more; welcome to Vermont. America’s second-least populated state is known for its two most important exports: maple syrup and Ben & Jerry’s ice cream!
Stowe is a small but characterful town, home to a plethora of independent businesses including Shaw’s General Store and Smugglers’ Notch Distillery. Taking a walk down Main Street, you’ll pass a tempting selection of shops, as well as the Stowe Community Church, easily identified by its bright white exterior and tall spire.
A short drive away you’ll reach the place the von Trapp family identified as a close match for their native Austria. Owned by the clan that inspired the Sound of Music, the Von Trapp Family Lodge has been welcoming guests for over 70 years. It is a perfect blend of old and new, featuring well-maintained guest rooms and framed reminders of the family history decorating the corridors.
The Ben & Jerry’s factory is also close by, and a short tour will take you through the factory and exhibits to the gift shop and ‘flavour graveyard’. If you’ve ever noticed your favourite flavour disappear from supermarket shelves, it is probably languishing in its own marked grave! The attached scoop shop is also a great place to taste new flavours that are not yet available to buy.
Today you’ll be heading south to the Green Mountains, the range behind Vermont’s nickname, “The Green Mountain State”. On your way out of Stowe, you’ll pass an exit for Moss Glen Falls, definitely worth a short detour. After an easy 10-20-minute hike you’ll be greeted by one of the views that has come to define Vermont; a beautiful waterfall with crystal clear swimming pools below.
Back on the road and heading south, it won’t be long until you can make out some magnificent peaks on the horizon. Mount Mansfield is the tallest at 4,393ft, with a summit said to resemble a human face (but I couldn’t make it out!). Killington Peak should also be visible, popular in winter for its ski resort, as well as Mount Ellen and Camel’s Hump.
You can hike or take a gondola/cable-car up Mount Mansfield for stunning panoramic views of the surrounding mountains. Camel’s Hump also features a well-regarded loop hiking trail with moderately challenging rocky scrambles.
Hildene, the Lincoln Family Home is located in Manchester within the Green Mountains and is a nice stop off for those interested in history. This was once the summer home of Robert Todd Lincoln, the eldest son of the 16th US President. Home to a treasure trove of artefacts, inside you can find one of Lincoln’s famous top hats, original family furniture and even a 1903 railway car.
Following the Green Mountains into Massachusetts you’re heading into The Berkshires. A year-round cultural and scenic destination, this region, roughly the size of Rhode Island, has been a popular holiday spot for over 150 years.
Especially well-known for the arts, the Berkshires is home to several galleries and performance venues. The Norman Rockwell Museum (Stockbridge) holds the world’s largest collection of Rockwell drawings and paintings, such as his ‘Triple Self Portrait’. Tanglewood in Lenox hosts the Boston Symphony Orchestra in summer and the Boston Pops throughout the year, providing performances from world-renowned conductors, soloists and musicians.
In Pittsfield, the Hancock Shaker Village keeps the memory of the colonial Shakers alive, with 20 historic buildings and a working farm and garden. The subject of a 2025 film with Amanda Seyfried, Ann Lee was considered a mother of the movement, bringing her followers to the American colonies in 1774. The village was in use until the 1960s, when it was transformed into a living museum.
In addition to cultural sights, you are guaranteed to be surrounded by beauty at every turn in the Berkshires, and there are plenty of natural attractions too. Mass Audubon Pleasant Valley Wildlife Sanctuary is a 1,100-acre wildlife sanctuary along the slopes of Lenox Mountain, featuring seven miles of hiking trails and the chance to spot black bears, white-tailed deer, and beavers.
You’re back on the road for one last long drive to the ‘Ocean State’ Rhode Island. Newport bound, get ready for some memorable coastal views and Gilded Age architecture.
The 3.5-mile Cliff Walk is the perfect way to see both sides of Newport, with panoramic ocean views, and the opportunity to spot opulent Gilded Age mansions like The Breakers and Rough Point. By car, you can also take the iconic Ocean Drive along a scenic route for breathtaking Atlantic views, historic mansions, and rugged coastline.
Take a walk down Thames Street in downtown Newport to appreciate the colonial-era buildings and cobblestone streets, and take time to pop into some of the shops, bars and restaurants as you go. The Mooring Seafood Kitchen & Bar is one of Newport’s top eateries, and trying a Bag of Donuts (lobster-shrimp fritters) will certainly not disappoint.
When it comes to visiting the Newport Mansions, you have a few to choose from, but The Breakers must be at the top of your list. This famous, 70-room Vanderbilt palace was built in 1895, influenced by Italian Renaissance design. The Elms is another top choice; a 1901 mansion modelled after the French Château d’Asnières. In addition to the opulent interiors and restored formal gardens, there is a ‘servant life’ tour available, offering a glimpse behind the curtain at the people who kept these grand houses running.
Fresh from your visit to the grand homes of yesteryear, you’re on your way to another summer retreat with a legacy of popularity. Running at a slightly slower pace than Newport, Cape Cod is a rural peninsula with more of a nature-focus and some beautiful beaches. Here you’ll find a few charming towns including Provincetown, Chatham, and Falmouth.
Provincetown is a cultural hub, with its own historic art colony and lively LGBTQ+ spaces. A guided 4×4 excursion through its distinctive dunes is a must-do, and if you’re in season, you may be able to spot migrating humpback and finback whales.
Chatham is more of a traditional New England beachside escape, with its own maritime history and famous lighthouse. History aficionados can find out more about the seafaring past at the Atwood Museum, and for those who’d rather be on the water, seal tours operate around the harbour.
Slightly livelier than Chatham is Falmouth, although its beaches are equally unspoilt. The Shining Sea Bikeway is a 10-mile trail that helps you make the most of the coastal views, but exploring the village shops and Main Street is a great way to spend an afternoon.
For your final stop you have a choice of two celebrated New England islands. Both offer a generous dose of New England charm and are easily explored by foot or bicycle.
Martha’s Vineyard is an affluent island just south of Cape Cod. With 6 distinct towns and 120 miles of shoreline to explore, there’s a lot to keep you busy here. Oak Bluffs in the east is a perfect place to start, with its colourful 19th-century ‘gingerbread cottages’ lining the streets. Ocean Park and the nearby Flying Horses Carousel have been delighting visitors for over a century and remain highlights of any trip to the island. To the west you’ll find more peaceful nature trails and the colourful clay cliffs of Aquinnah. Martha’s Vineyard was famously the filming location of Spielberg’s Jaws in the 1970s, and Edgartown in the east served as the centre of the fictional Amity Island. Today you can take special Jaws tours around the island to see a few featured locations.
Nantucket Island is about half the size of Martha’s Vineyard and is a designated National Historic Landmark District. More walkable and with attractions more centrally located than its neighbour, Nantucket is a good choice for those looking for a slightly more relaxed pace and more of a history focus. The Nantucket Whaling Museum tells the story of the island’s maritime history, and quaint villages like Siasconset allow you to follow in the footsteps of the late 19th-century artists and actors who selected it as their New England retreat. Nantucket’s historic status can make stays expensive, but on a day trip you’ll get a taste of this pricey island, without spending too much.
After a final night on Cape Cod, it’s time to head back to Boston and complete your New England loop. On the way you might want to make a stop in Plymouth, the original Pilgrim landing site in 1620. There you can visit Plymouth Rock, enclosed within its own granite portico, and the Mayflower II, a reconstruction of the famous ship.
Re-entering Boston, you’ll have successfully completed a 1,200-mile loop around New England. I’m sure by now you, like me, will be full of both experiences… and seafood!
You’ll also be faced with a similar dilemma – there’s still so much of New England to explore, and different seasons to experience. My next goal is to be in Salem for Halloween – where will you be?
Get in touch with our America Experts to start planning your adventure today.
Sarah Sutton is the Social Media Manager at Freedom Destinations and can often be found scrolling TikTok if she’s not boarding a flight. She has spent time living in Europe and has travelled in South East Asia, Australia, America and Canada Her next dream destination is Japan.
