THE ITINERARY

I scored a two week trip around the six states of New England thanks to a car rental from Hertz (other car rentals companies are available) that I booked from the UK about ten months earlier.

Navigating anti-clockwise, the road trip would kick off with me barreling north out of Boston, steering through various towns in Massachusetts before plunging into the coastal city of Portland, Maine. From there I’ll veer west into the wilderness of New Hampshire and push further into the landscapes of Vermont. But wait! The adventure doesn’t stop there; turning the car due south out of Vermont, navigating my way back through Massachusetts, and into Connecticut. Just when you think it was over, I’ll swing the car east into the minuscule state of Rhode Island, only to blast further east towards the enchanting Cape Cod, Martha’s Vineyard for those 1975 ‘Jaws’ location spots, veering north into Provincetown, before finally spinning 360⁰  to make my grand return to Boston – 1100 miles later.

Sure, two weeks isn’t nearly enough to really soak in all this part of America, but since I was short on time, I improvised!

• ROUTE HIGHLIGHTS:
• MASSACHUSETTS STATE
• Salem – get those spooky vibes!
• Gloucester, and check out the Eastern Point Lighthouse
• MAINE STATE
• Portland with its iconic Portland Head Lighthouse
• Kancamagus Highway in New Hampshire – stunning drive!
• NEW HAMPSHIRE STATE
• Jackson and those charming covered bridges in New Hampshire
• VERMONT STATE
• Montpelier and Stowe, Vermont – small-town charm
• Burlington, Vermont – perfect for a chill day
• CONNECTICUT STATE
• Hartford, Connecticut – city with some history
• RHODE ISLAND STATE
• Newport, Rhode Island – coastal beauty
• CAPE COD PENNINSULA
• Falmouth and Martha’s Vineyard, Cape Cod – Jaws galore
• Provincetown, Cape Cod – artsy town with a view
• Boston, Massachusetts – a classic stop!

MASSACHUSETTS – Salem

Heading north out of Boston along highway 1A is Salem, located about an hours drive away, was founded in 1626 by Robert Conant whose statue still remains right in the downtown area.

This quirky yet mysterious place has a strong history tying back to the 1693 Witch Trials where over 200 people were accused of being involved with witchcraft.

While many were accused, 20 people were executed. With the lack of technology and understanding of physical illness and mental health issues, doctors made alternative diagnoses. They insisted that the only explanation is that these girls were possessed by the devil, therefore being classified as witches performing witchcraft.

It was only a year later, after the hangings, that the witch trials were deemed as unlawful. A very tragic and unfortunate period of time. It’s no doubt that hundreds of thousands continue to visit Salem to pay their respects and learn about these bizarre circumstances. My visit to Salem was only for the morning but I packed a lot into those few hours! I parked at ‘Waterfront Garage’ multi-story car park. Fortunately, the parking that day was free of charge!

What does Salem offer?

Titled ‘the most beautiful street in Salem’, you’ll want to stop by to see all of it’s magic and beauty especially if you’re visiting during the Autumn.

Nestled amidst historic neighborhoods Chestnut Street stands as a living testament to the city’s architectural legacy. Take a stroll through this tree lined avenue adorned with impeccably preserved Federal and Georgian-style mansions.

The Bewitched Statue

The Bewitched Statue is a prominent landmark commemorating the famous 1960s television show ‘Bewitched’ that was set in the fictional town of Westbridge but had strong ties to Salem. The statue features the character Samantha Stephens played by actress Elizabeth Montgomery, who was a good natured witch married to a mortal.

The Witch House

The Witch House, owned by Jonathan Corwin, one of the judges of the Salem witch trials, is the only standing building in Salem with direct ties to the witch trials. This building is referred to as ‘first period colonial architecture’ which refers to any structure built between 1620-1720.

The Witch House operates as a museum, offering guided tours and showcases a collection of period furniture, tools, and artifacts, providing visitors with a glimpse into daily life in colonial Salem.

Old Burying Point Cemetery

Old Burying Point Cemetery is one of the oldest cemeteries in the United States and holds historical significance, dating back to 1637. The cemetery contains the graves of many notable individuals from Salem’s early history, including Mayflower passengers, military figures, and prominent residents from the colonial and Revolutionary War eras.

It’s also the final resting place of several notable figures, including Judge John Hathorne, a key figure in the Salem Witch Trials; Jonathan Corwin, a judge during the witch trials; and Mary Corey, the wife of Giles Corey, who was pressed to death during the trials.

Ropes Mansion

The Ropes Mansion, also known as Allison’s House in Hocus Pocus, is one of the most architecturally stunning houses in Salem. It was built in 1727 by Samuel Barnard, a wealthy merchant. The mansion is best known for its association with the Ropes family. In 1768, Judge Nathaniel Ropes, a prominent figure in Salem, purchased the house.

Max and Dani’s House

An iconic and must see house in Salem located at 4 Ocean Avenue. The famous home of Max and Dani from Hocus Pocus.

Salem old Town Hall

Old Town Hall was built in 1816-1817 and was designed by Charles Bulfinch, a prominent architect who also worked on the Massachusetts State House in Boston.

It’s also the filming location where Max and Dani from Hocus Pocus ran up the steps of the Hall at the Halloween party to warn their parents about the Sanderson Sisters.

Where to eat?

My stop in Salem was only for the morning but I made sure I stopped for food before continuing the journey deeper into the state of Massachusetts.

O’Neills Irish Bar – oneillsofsalem.com

Located at 120 Washington Street, offers great wholesome meals and drinks at reasonable prices all served by the friendly charm of the tavern staff.

MASSACHUSETTS – Gloucester & Eastern Point Lighthouse

The drive from Salem to Gloucester took roughly 30 minutes towards an area known as Cape Ann. Gloucester is a historic seaport home to the Eastern Point Lighthouse that is no longer open to the public but can still be walked around. There is a small free car park located at the foot of the lighthouse.

The Eastern Point Lighthouse was built in the 1880s and is currently an active lighthouse.  On the property you will also find: the oil house, radio beacon, fog horn building, and Dog Bar Breakwater.  Access inside the fence is forbidden, however there are good views of the light station from the exterior.

Unless you wish to stop for refreshments this town could be an easy stop-off along your journey. I spent about two hours here.

MAINE – Portland

Portland in Maine was the second State of New England to explore. From Gloucester the drive took an hour and a half north along the I95 highway.

Portland boasts a small town feel that is beloved by its residents.

Portland epitomises the deep-Northeastern experience conjuring visions of fishermen walking streets straight out of an L.L. Bean catalogue. That image of Portland still remains – lighthouses, lobster rolls and plenty of opportunities to use the word ‘cute’.

I was lucky enough to visit Portland in September and I have to say I fell head over heels. I stayed at the Canopy by Hilton Hotel right on the waterfront. The location is fantastic. The hotel offers a valet car park service for $20 p/d. Here are my picks for the best things to do in Portland, Maine.

What to see in Portland

Portland is super easy to navigate and you’re always just a hop away from a spot to grab a bite, have a drink, or shop for some cool souvenirs.

Portland Head Lighthouse

If you like history and culture you will probably want to snap a picture of the Portland Head Light. Located about 5 miles away, it’s the oldest lighthouse in Maine and one of the most photographed. Grab an Uber or drive out to Fort Williams Park (Parking is $2 per hour) to check it out up close, along with the namesake fort. It’s not an entire day’s worth of an activity, but it is a cool photo opportunity.

Portland Observatory

Located at 138 Congress Street the Portland Observatory is a historic maritime signal tower built in 1807. It is the only known surviving tower of its type in the United States. Tickets for adults cost $10 with guided tours in the morning, and self tours in the afternoon.

The Waterfront and Commercial Street

The waterfront and Commercial Street beautifully align, offering a vibrant mix of taverns, charming souvenir shops, market stalls, and delightful eateries, all boasting stunning views across the harbour. It’s a wonderful area to take a leisurely stroll after enjoying a delicious meal.

Where to eat?

Portland is a delightful treasure trove for food lovers, perfect for enjoying a bite, snack, or drink. The city is filled with charming independent eateries, predominantly nestled along the vibrant Wharf and Fore Streets, inviting everyone to indulge in unique culinary experiences. If you like seafood then Portland is heaven.

Portland Lobster Company – portlandlobstercompany

Located right on the waterfront there’s this awesome spot that serves up seafood specials and their famous lobster roll. In the evenings, they even throw in some live music to amp up the vibe!

Luke’s Lobster – lukeslobster.com

Located at Portland Wharf – It’s a bit on the pricey side, but the views across the harbour are totally worth it!

Holy Donut – theholydonut

Located on Commercial Street at the waterfront, stop for a sweet treat. These doughnuts are made from potatoes glazed with various toppings. Delicious and filling!

Duckfat – duckfat

Located at 43 Middle Street, a fantastic yet popular brewery with good food options. They serve up sandwiches like the next level Overnight Duck Confit with duck fat-fried frites and donuts.

Becky’s Diner – beckysdiner.com

If you’re wandering down Commercial Street on the waterfront, you have to check out this awesome spot for food! Breakfast here is a must— think hearty meals that’ll kickstart your day. It’s super popular, so you know it’s good. And don’t forget to grab a souvenir mug while you’re at it!

STATE OF NEW HAMPSHIRE

The continuing leg of my New England trip would see me drive west from Maine to New Hampshire (the third State on this trip), heading straight for the cute little mountain town of Jackson.

This part of the trip was all about searching for those beautiful covered bridges that are peppered all over the state.

The drive from Portland to Jackson is only 65 miles. In Jackson, I had the delightful experience of staying at The Wentworth Inn for the night. The hotel provides free car parking, nestled in stunning surroundings that enhance the beauty of the geography.

There isn’t a huge amount to do in this sleepy town. It’s very much a hiking area for the Huntington Ravine and Tuckerman Ravine Trails. For me, it was a stop over for the next segment of the drive west into Vermont.

Wentworth Inn – Jackson

Where to eat?

Wildcat Inn and Tavern – wildcattavern.com

Located on Main Street, try Wildcat Inn and Tavern for delicious foods and relaxed drinks.

VERMONT STATE

The drive westwards from Jackson, New Hampshire to Burlington, Vermont along the stunning Kancamagus Highway and route 302 spans approximately 145 miles.

This exhilarating journey also includes the charming towns of Montpelier and Stowe, offering ample opportunities to capture breathtaking photos of the Kancamagus Highway and the iconic Cold Hollow Cider Mill.

What to see in Vermont?

Kancamagus Highway

This is a portion of NH Route 112 spanning east to west from Lincoln to Conway, and out to the State line. The 34.5 mile drive is a recognised National Scenic Byway, offering travelers natural beauty in addition to being considered one of the best autumn foliage viewing areas in the world.

The byway winds across the state through the heart of the scenic and mountainous White Mountain National Forest. Along the route several scenic vistas are plotted along the road side offering remarkable views of the White Mountains, the Swift River, Lower Falls, Sabbaday Falls, and the Rocky Gorge.

A place to eat on the Kancamagus Highway

As the highway meanders descending the mountains towards the the town of Lincoln, located on Main Street (technically this is still New Hampshire) is a popular little rest stop called ‘Moose on the run Cafe’ that offer indoor/outdoor seating, meals and a well earnt drink. I stopped for a chicken Caesar salad which was extremely filling.

Montpelier

Not far from where route 302 seamlessly connects with I89 to Burlington lies the vibrant town of Montpelier, the illustrious capital city of Vermont.

The impressive 1859 Vermont State House is a striking gold-domed Greek Revival building, showcasing an exceptional array of decorative arts and fine collections. At the adjacent Vermont History Museum, a captivating multimedia exhibit and mural brilliantly celebrate the state’s rich history. Nearby, the expansive and lush Hubbard Park boasts meadows, a stunning birch grove, and a formidable stone observation tower that invites exploration.

A Place To Stop in Montpellier

I spent a few hours here exploring the city before continuing the road trip. I managed to park the car for free along a residential street. I did manage to stop for a drink at the ‘Three Penny Taproom’ located on 108 Main Street, which I would recommend.

Ben and Jerry’s – benjerry.com

Just 13 miles outside of Montpelier, you’ll stumble upon the Ben and Jerry’s ice cream headquarters. This is where it all started back in 1985, and they’re still cranking out over 350,000 pints every single day! On-site, there’s also a scoop shop and gift shop. Tours are available, but heads up—it gets super busy, so you might have to hang tight for a while. It was so busy when I arrived I literally took a photograph and left.

Cold Hollow Cider Mill – coldhollow.com

Two miles up the road from Ben and Jerry’s lies the enchanting Cold Hollow Cider Mill, a former dairy barn transformed into a delightful cider haven! This charming cider farm invites visitors to explore its captivating offerings, from guided tours to leisurely strolls around the cafe, unique shop filled with all kinds of delightful souvenirs and delectable consumables, to the irresistible bakery. Treat yourself to a steaming hot or refreshingly cold apple cider drink—it’s an experience, even if it comes with a price tag!

Stowe

Located in northern part of Vermont state, Stowe feels a lot like a postcard, and you’ll find covered bridges, a wonderful little Main Street all surrounded in the Summer by emerald hills and sapphire skies.

Stowe was chartered in 1763, but its first settlers didn’t arrive until 30 years later. I was here for a few hours exploring but did manage to locate some free parking along the high street.

Stowe has a small but lovely Main Street with really great shops and eateries. Be sure to spend some time meandering through the storefronts because chances are you’ll find a few things you can’t leave without.

A Place to stop and watch the world pass by in Stowe

If you’re in the mood to take a break and grab a drink, you should check out Stowe Public House at 109 Main Street. They offer drinks and tasty food, plus some awesome balcony seating or comfy chairs out on the lawn.

My time in Stowe was brief but just enough time to explore the town and rest before continuing the drive out towards Burlington for the night, 45 minutes away along I89.

Burlington

The final and overnight stay on the drive from New Hampshire to Vermont is the city of Burlington – the largest city in the state, and the home to the University of Vermont. Burlington is only a rough 45 miles drive from the Canadian border sat on the shore of Lake Champlain, looking across to upper state New York.

The city offers lake views and local cider to pedestrian friendly streets and mountain backdrops, Burlington, is one of the best stops I made on this New England road trip.

Where to stay?

With a car in tow, I was mindful to choose hotels on this trip that provided free or affordable parking options. I happily stayed at the ‘Homewood Suites by Hilton’, that offered a delightful breakfast (unlike many American hotel chains), easy access from I89, and a charming 40 minute walk to downtown that showcased the beautiful University of Vermont along the way.

What does Burlington offer?

If you only do one thing in Burlington, start at the waterfront. The views of Lake Champlain and the Adirondack Mountains across the water are unforgettable.

• Burlington’s waterfront is truly a gem that distinguishes it from everywhere else! It’s one of the rare walkable cities in the U.S. where breathtaking lake views blend seamlessly with the majestic mountain backdrops in every direction. While many cities boast market streets and vibrant breweries, few can claim the remarkable beauty of sitting right on the shores of Lake Champlain, with the stunning Adirondacks just across the water. It’s nothing short of spectacular!

Walk Church Street

This pedestrian only street is clearly the beating heart of downtown Burlington.

• Check out local shops
• Grab a bite or drink at numerous outdoor patios
• Don’t miss the iconic view down Church Street to First Unitarian Church

University of Vermont

Founded in 1791, the University of Vermont is the States oldest place of education. Take a stroll around the gardens and marvel at the architecture.

Where I stopped for food

There are numerous fantastic spots to indulge in delectable cuisine and enjoy a few beers, particularly along Church Street. However, I confidently chose the ‘Farmhouse Tap and Grill’, located on Bank Street. The food is abundant and offers a wide selection. I went with the meatloaf – simply scrumptious!

CONNECTICUT – Hartford

Buckle up, as this drive is by far the longest—235 miles of relentless asphalt stretching south from Burlington, Vermont to Hartford, Connecticut, where the highways I89, Highway 5, and I91 dare you to experience the thrill of the open road.

With art galleries, lush gardens, and historic buildings, there are so many amazing things to do in Hartford, Connecticut.

Packed with historic attractions and fascinating museums, Connecticut’s capital is one of the most captivating cities in the United States. Hartford has proudly hosted literary giants like Mark Twain and distinguished campaigners such as Harriet Beecher Stowe, and this vibrant cultural legacy continues to enrich the city today, making it a truly inspiring place to explore.

Where I stayed

I spent one night at the Doubletree by Hilton were car parking was provided for a small fee by the hotel. The location is great for Hartford city centre and Pratt Street, and linking directly to PeoplesBank arena.

What does Hartford offer?

Hartford is very much a business city and to my surprise it was generally very quiet over the weekend in which I stayed.

Wadsworth Art Museum

I must confess, art museums have never truly captured my heart, but when a sudden thunderstorm compelled me to seek refuge, my perspective shifted. This gem, the oldest continually operating art museum in the United States, boasts an exterior that is nothing short of breathtaking, drawing me in with its undeniable beauty. It’s free to enter and was actually impressed. Thank you thunderstorm!

Mark Twain House

A visit to Hartford allows you to step back in time and walk in the footsteps on one of America’s literary greats: Mark Twain. The Mark Twain House and Museum is dedicated to the author’s life and works and is set in his former residence. That’s the very house in which he wrote classics including The Adventures of Tom Sawyer, The Adventures of Huckleberry Finn and the Prince and the Pauper.

Connecticut State Capitol Building

With its beautiful gold-plated dome, the Connecticut State Capitol is a national historic landmark and a must-see on any trip to Hartford. Often confused with the Old State House, the current Capitol was completed in 1878, and represents the unique fusion of Victorian Gothic style characteristic architecture.

 

Bushnell Park 

Bushnell Park, a gem among the first publicly funded parks in the US. Take opportunity to enjoy a delightful ride on its stunning vintage carousel. I visited in September were the city’s breathtaking foliage was on the golden turn.

Pratt Street

Pratt Street is a 200 year old hub of entertainment lined with bars, cafe and restaurants off Trumbull Street. Find yourself some delicious food, or watch a game at one of the sports bars. I did find a lovely bar called the Sunberry that offers Korean style food and IPA beers.

Another great venue for food, located at 25 Front Street is Bears Smokehouse and Barbeque. They offer hearty Kansas style smoked BBQ meals and thirst quenching beers. I ordered the pork burnt ends, baked potato and an IPA beer – Chef’s Kiss!

New Haven

The next sector of the road trip was to head south out of Hartford along I91 towards New Haven, before turning east towards Newport, Rhode Island. New Haven is a city in the state of Connecticut located on New Haven Harbour on the northern shore of Long Island Sound.

It’s home to Yale University, founded in 1701 and the Natural History Museum.

Yale University is the third oldest institution of higher education in the United States. Yale is definitely worth spending a couple of hours exploring. Why not pick-up some souvenirs in the official Yale University college shop?

Natural History Museum

Whilst in New Haven, you absolutely must carve out time to visit the Peabody Museum of Natural History at Yale University, a gem among the oldest and largest natural history museums in the world!

Founded by the visionary philanthropist George Peabody in 1866, this museum showcases a breathtaking array of historic natural displays. My absolute favorite? The awe-inspiring dinosaur exhibits that ignite the imagination and transport you to a time when these magnificent creatures roamed the earth!

RHODE ISLAND – Newport

The fifth gem on the New England road trip, Rhode Island, is a delightful little state stretching a mere 37 miles from west to east. Yet, in its petite size lies an overflowing abundance of charm.

Nowhere is this more evident than in the coastal town of Newport. Nestled on the shores of Aquidneck Island, Newport is a thriving little city that’s beautiful to visit.

Easily reached by a number of bridges connecting the island, it’s the kind of place that’s well worth visiting for a day when road tripping the east coast. 

Newport has become one of my absolute favourite places in the United States. Newport is a town known for its historic gilded age mansions and historic charm dating to the 17th century. It’s a wonderful destination to put on your USA itinerary, especially if you’re here for the summer.

The best course of action is simply exploring Newport on foot meandering the streets brimmed with cafes, taverns, restaurants and souvenir shops. Make time to explore Bowens Wharf where fishing boats and nautically named seafood taverns are found.

What else does Rhode Island offer?

Ochre Point Avenue and The Breakers

Be sure to check out Ochre Point Avenue and The Breakers, a vast Vanderbilt mansion that’s too amazing to miss. Built back in the 1800s, it was symbolic of the Vanderbilt’s wealth. You can purchase tickets for The Breakers Mansion for $32.

With around 70 rooms and a colossal three story dining room that’s a total masterpiece. The whole mansion is a work of art! 

Afterwards, step out of The Breakers and follow the iconic Cliff Walk that heads around the shoreline and bays here. The views from here are totally stunning and it’s such a gorgeous spot to visit.

White Horse Tavern

Although I didn’t have chance to check it out, I would recommend hitting up the White Horse Tavern, the oldest tavern in the U.S. Located on Marlborough Street and founded in 1673 and is an awesome spot for dinner. If you’re a fan of clam chowder, this place might be for you!

International Tennis Hall of Fame

A mile out of Newport lies the International Tennis Hall of Fame. If you’re a true tennis enthusiast this gem is an absolute must on your Rhode Island road trip. Strolling through its grounds is completely free, but remember, working tennis venue where locals don their pearly whites, passionately battling it out on the courts. If fortune looks upon you (as it did for me), you might just snag a free parking spot on the street for two glorious hours! Score!

MASSACHUSETTS – Cape Cod

Cape Cod, a hook-shaped peninsula making up part of the state of Massachusetts, is a popular summertime destination.

It’s the site of quaint villages, seafood shacks, lighthouses, ponds and ocean beaches.

The large towns of Falmouth and Hyannis is the first stop where ferries depart to the islands of Martha’s Vineyard and Nantucket, but, ensure Provincetown features highly on the hit-list of places to visit on the Cape. Check out my separate blog on Provincetown.

Red Inn, Privincetown

Cape Cod, and the state of Massachusetts, makes up the sixth and final state of the New England road trip. From Rhode Island I headed east along I195.

Where I stayed

I happily chose to stay in the town of Falmouth on the lower Cape, a decision driven by the most convenient ferry route to Martha’s Vineyard. For two delightful days, I experienced what I can only describe as pure magic at Autocamp by Hilton. It was nothing short of an extraordinary. This ‘hotel’ is a whimsical campsite adorned with charming silver bullet caravans, cosy tents, and rustic log cabins to immerse yourself in nature. I opted for the silver bullet caravan—what a brilliant choice! Best of all, the parking is free.

Falmouth

From the sheer abundance of camp sites it’s evident that Falmouth is a beloved holiday haven on the stunning southern Cape. With its breathtaking beaches and charming villages it’s clear this destination offers a slice of paradise that truly caters to every taste and desire. Falmouth, in addition, is a great anchor point for the ferry terminal to Martha’s Vineyard.

What can Falmouth offer for two nights?

Main Street in Falmouth is a charming downtown area that offers a wide range of shopping, dining and entertainment options.

The street is lined with historic buildings, many of which date back to the 19th century and feature beautiful architecture.

Visitors can browse through a variety of unique shops, art galleries and antique stores or grab a bite to eat at one of the many restaurants and cafes that line the street.

Main Street is also home to the Falmouth Museums on the Green that features exhibits on the town’s history and culture and various events throughout the year.

Where to eat

There are so many places to stop for a bite to eat you will not be short of choice.

Tap City Grille – www.tapcitygrille.com/falmouth

Located at 285 Main Street, this gem serves up incredibly generous portion sizes alongside exceptional cocktails, all within an inviting and relaxed atmosphere that makes every visit feel like a special occasion.

Martha’s Vineyard Island

On a day trip to Martha’s Vineyard you can explore Oak Bluffs, its colourful cottages and the historic Flying Horses Carousel. Visit Edgartown to wander the quaint streets lined with elegant captain’s homes and see stunning views from the Edgartown Lighthouse.

I used the Steamship Authority from Woods Hole to Vineyard Haven. Walk-on, round-trip tickets are less than $30 (GB£22.20), and you can get around the island with a cheap bus day pass. Or, bring your own vehicle for $128+ (GB£95+).

I confidently opted to take the ferry on foot and rent a car once I arrived on Martha’s Vineyard. The Steamship Authority excels at coordinating a seamless park-and-ride experience, complete with a shuttle bus to the ferry terminal. Since parking isn’t available at Woods Hole, I left the car at Palmer Avenue Lot at 286 Palmer Avenue, Falmouth, for a fee of $25 (GB£18.50) per day, that includes shuttle bus access. I boarded the 7:30 AM ferry from Woods Hole, arriving promptly at Vineyard Haven.

Martha’s Vineyard is a paradise for devoted ‘Jaws’ enthusiasts, especially those who revel in the thrill of the iconic 1975 film. You can make a day of it driving the island for those location spots.

The highlights of this day trip

• Menemsha Beach
• Aquinnah Cliffs
• Gay Head Lighthouse
• Edgartown
• Jaws Bridge

Jaws location spots

Where to eat?

After such an early start to catch the ferry I was determined to grab a quick breakfast, fully aware that I had only 8 hours on the island before the return ferry.

In Tisbury, just on the edge of Vineyard Haven, there was a lovely sandwich shop called ‘7a Foods’ that warmly welcomed everyone with a delightful assortment of hot and cold sandwiches, along with refreshing drinks to perfectly complement. Parking is free. There is a small General Store adjacent to the shop should you require any drinks or snacks for the car.

The second pit-stop was in Edgartown (found free parking down a residential area). I decided to stop for a drink at ‘The Wharf’, located on Main Street near the harbour. Inside is warm and cosy with a bar area with TVs playing sports for some drinks and snacks, or the attached restaurant. It does get busy so be prepared to wait.

A day trip around Martha’s Vineyard is nothing short of an exhilarating adventure! For me, it unfolded as an action packed itinerary filled with iconic Jaws location sites and every moment was absolutely worth it. As the sun began to set, I capped off the day with a breathtaking ferry ride across the Vineyard Sound, back to Woods Hole from Oak Bluffs, a perfect finale to an unforgettable experience.

Provincetown

The next sector of the New England road trip took me a further 68 miles around the arm of the Cape, along highway 6, from Falmouth to Provincetown. Provincetown is located at the very tip of Cape Cod in Massachusetts, roughly 115 miles from Boston.

Often referred to as “P-Town”, it’s a famously inclusive destination beloved by the LGBTQ+ community and open-minded travelers.

There’s an energy here that blends beachy charm, rich history and year-round festivities, making it much more than just another seaside stop.

I’ll refrain from writing too much here about Provincetown as I have a dedicated blog about this charming town from a previous visit.

Where I stayed?

Provincetown was the penultimate stop before the drive back to Boston, marking the bittersweet end of my unforgettable New England road trip. Having experienced the charm of P’Town before and fully aware that it lay over 115 miles from Boston, I eagerly decided to stay at the perfect halfway point, enjoying a night in delightful Hyannis; just an hour south of Provincetown. I settled into the dated yet comfortable rooms of the Doubletree by Hilton, savouring the free parking space.

Boston

On the final day of the New England road trip, I woke with a heavy heart, cherishing the amazing experiences I had gained over the past two weeks as I made my way back to Boston, where it all began. The drive took me west along Highway 6 off the Cape, onto Highway 3, and ultimately I93 at Quincy back to Boston Logan Airport, where I would drop off the car rental and reflect on the incredible adventure.

Boston is a historic city home to old centuries old colonial buildings and a strong link to the country’s founding (the Boston Tea Party happened here in 1773)

Bostonians are undeniably proud of their city and seize every opportunity to showcase that pride. This city is steeped in remarkable history and stunning beauty. Boston exudes the charm of a large town rather than the hustle of a metropolis. Friendly locals greet you, die-hard sports fans passionately support their teams and you’ll discover vibrant bars, excellent restaurants, and an abundance of American history waiting to be explored.

Like Provincetown, Boston holds a special place in my heart having visited it countless times, each journey fueling my passion for this city, that I celebrate in my dedicated blog filled with all kinds of things to do and see.

Where I stayed?

Boston bursts with an array of places to stay, and while the city isn’t the most budget friendly option, the experience is undeniably unforgettable. I chose the vibrant decor of the YOTEL Boston at the Seaport. The rooms may be straightforward, but the location is simply unbeatable—just a delightful 5 minute stroll from the Boston Tea Party Museum, and a 15 minute stroll to the bustling Quincy Market.

FINAL THOUGHT

Wow, What a trip!

Two weeks immersing into the diverse landscapes of 6 very captivating states of New England was nothing short of exhilarating!

My heart overflowing with memories, sensory delights, and warm encounters with welcoming locals. This region pulsates with diversity, seamlessly blending energy of the urban southern states with the serene beauty and untamed wilderness of the north.

As time was so precious I couldn’t afford to take each day as it came, in fear of wasting too much of it. I heavily researched churning over blogs, maps and itineraries in search what each state had to offer, executed the route via Google maps, and made tweaks. There was very little margin for error…. and it worked. It really worked. Of course, some eateries or attractions were edited throughout the road trip after speaking to locals and taking up their recommendations and alternatives, most often welcomed.