14-Day New England Road Trip Itinerary - Travel for Your Life

14-Day New England Road Trip Itinerary

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My favorite way to discover a new destination is by going on a road trip, and I had my sights set on New England. This historic region has its roots in America’s foundation and has many of its first resort towns. With its sandy beaches, colourful foliage, crystal-clear lakes, and craggy peaks, New England has immense natural beauty.

Thanks to its relatively small size, New England is one of my top picks for road trips in America. You can drive through some states in a single day, and there’s almost always a convenient place to stop. From the sea to the mountains, the scenery changes before your eyes to create an unforgettable vacation.

To get the most of your New England road trip, I devised a 14-day itinerary that takes you through seven beautiful states. Our road trip route takes us through all six of the traditional New England states, and I also added a couple of days in New York State. Between the beaches, mountains, and enchanting towns, I think this itinerary hits a little of everything.

Fill up the car, buckle up, and get ready for the ultimate New England adventure!


14-Day New England Road Trip Itinerary

Starting Destination: Boston | Day 1 – Boston (MA) to Cape Cod (MA) | Day 2 – Cape Cod (MA) | Day 3 – Cape Cod (MA) to Newport (RI) | Day 4 – Newport (RI) to Litchfield (CT) | Day 5 – Litchfield (CT) to Adirondacks (NY) | Day 6 – Adirondacks (NY) | Day 7 – Adirondacks (NY) to Green Mountains (VT) | Day 8 – Green Mountains (VT) | Day 9 – Green Mountains (VT) to White Mountains (NH) | Day 10 – White Mountains (NH) | Day 11 – White Mountains (NH) | Day 12 – White Mountains (NH) to Acadia National Park (ME) | Day 13 – Acadia National Park (ME) | Day 14 – Acadia National Park (ME) to Boston (MA) | Depart Logan International Airport


Starting Destination: Boston

One of America’s most historic cities, I thought Boston was a great destination to begin my New England road trip. As the region’s biggest city, Boston beams with culture, world-renowned universities, and American Revolution monuments. In particular, the Freedom Trail stood out as a fascinating attraction to visit museums and historic sites. Boston also has fantastic eateries, great craft breweries, shopping galleries, pulsating nightclubs, performing arts theatres, and harbour cruises. It’s a bustling metropolis, and I think it’s worth spending a few days here before hitting the road.

If you’re flying into Boston, then Logan International Airport is where you’ll arrive in the city. The airport is less than five miles from downtown Boston, and there are plenty of car rental agencies to find a vehicle. Rentals from the downtown Boston area are typically more affordable than those from Logan International Airport. The fastest way from Logan to downtown Boston is through Charlestown, North End, or South Boston Waterfront via water taxi. Boston also has a subway system, and taxis are available from the airport.

I would advise you not to pick up a car rental in Boston until you’re ready to depart for your New England road trip. Driving around Boston is extremely challenging due to winding roads, unexpected one-way streets, and GPS inaccuracy. Plus, parking fees across Boston are outrageously high and not worth just a few days in the city. If you’re on a budget, then this will quickly eat into your funds for the rest of your vacation.

Trust me; that wouldn’t be any fun. However long you wish to explore Boston, don’t pick up the car until the day you leave this amazing New England metropolis.


Day 1 – Boston (MA) to Cape Cod (MA)

To kick off my 14-day adventure, I decided to drive south of Boston to the sandy shores of Cape Cod. This popular summer retreat is about 1-2 hours from Boston, depending on your exact destination on the Cape. It was tough pickings where to stay in Cape Cod due to all the charming seaside towns on the peninsula. Sandwich, Chatham, Dennis, Eastham, and Provincetown are just a handful of my top recommendations. U.S. Route 6 is the primary thoroughfare through Cape Cod and provides a scenic drive across the peninsula.

Ultimately, I decided to drive the entire peninsula through Cape Cod National Seashore and stayed at vibrant Provincetown. Regarded as an artist haven, Provincetown enchants you with its pilgrim monuments, historic homes, art galleries, lighthouses, and pristine beaches. Commercial Street is where you’ll find fabulous seafood restaurants, and sunsets on Race Point Beach offer stunning portraits. After driving nearly 120 miles from Boston, it was the perfect spot to stretch my legs and hear the ocean waves.

Just south of Provincetown, the Atlantic side of the Cape from Truro to Chatham beckons surfers. With about 1,500 miles of coastline, Massachusetts has dozens of beaches to take your surfboard and Cape Cod features much of the best surf in Massachusetts.




Day 2 – Cape Cod (MA)

Before I left Massachusetts, there was one summer activity I had to do while staying at Cape Cod. From Provincetown, I embarked on a whale watching tour to watch these majestic animals in their natural environment. There are several whale watching tour companies based around Provincetown Harbor to host your voyage. Although whale watching season is from April-October, June-September is the best time to spot marine creatures.

On your cruise, you could see Humpbacks, Finbacks, Minkes, and dolphins. From the vessel, you’ll also have the chance to take incredible photos of the beaches and lighthouses of Cape Cod National Seashore. This 3-4 hour trip topped my highlights on the New England coast.

Although I wanted to explore the sea, the area has tons of outdoor activities on land as well.   Your options include bike trails, sand dune hiking paths, and woodland nature preserves. Before packing the car, dine on more succulent seafood and famous Cape Cod ice cream. There are a lot of fun things to do in Provincetown so even if outdoor activities is not your thing you wont get bored.

A tasty way to end a delightful day in Cape Cod!



Day 3 – Cape Cod (MA) to Newport (RI)

The next place on my road trip itinerary was the smallest state in America, Rhode Island. Despite its meagre size of 1,212 sq miles, Rhode Island packs many New England gems inside its borders. I could’ve spent more time exploring Rhode Island’s colonial towns, white-sand beaches, and beautiful architecture, but other states were higher on my list.

Around 2.5 hours from Provincetown, Newport was one Rhode Island destination I wanted to check out. This elegant resort town for the rich and famous dazzles visitors with its Gilded Age mansions and a yacht-filled harbour. The 10-mile Ocean Drive showed off spectacular seaside views and lavish homes dotting the Atlantic Coast. If you’d rather spend the day lounging on the beach, check out Easton’s Beach or Third Beach. Other attractions in Newport include The Breakers, Fort Adams State Park, and the Cliff Walk.

Providence, the Rhode Island capital, lies about 45 mins north of Newport. However, I bypassed the city life and stuck with the surreal coastal views before I ventured inland.



Day 4 – Newport (RI) to Litchfield (CT)

Instead of driving north back towards Massachusetts, I decided to head westward into Connecticut. Upon leaving Newport, I made a pit stop in the charming seaside town of Narragansett to admire those Rhode Island surf beaches one last time. My advice is for Rhode Island is to run straight to the sea; it’s such a relaxing place to be and one of the perfect romantic getaways in Rhode Island as well.

Once I entered Connecticut, it was time to start making my way towards the mountains and maybe stop at one of Connecticuts wineries on the wat. If you can’t get enough coastal charm, one Connecticut destination to stop is the seaport town of Mystic. Just a 45-50 minute drive down U.S. Route 1 South from Narragansett, Mystic is a delightful spot for lunch and shopping. Dine on seafood, stop by the famous Mystic Pizza, or have ice cream beside the drawbridge.

As I continued my drive through the Connecticut countryside, I came across an underrated New England gem. Tucked away in the northwest corner of Connecticut, the Litchfield Hills prepped me for future mountain views. The area beams with rustic towns, adorable farms, and trickling waterfalls. If you drove through this area in fall, the colourful foliage would take your breath away. This quaint section of Connecticut is made for nature lovers and offered way more than I expected. And given Connecticut’s small size, I made it here from seaside Mystic in under two hours.



Day 5 – Litchfield (CT) to Adirondacks (NY)

New York isn’t one of the traditional New England states, but it has some of the best mountain views in this region of America. The Adirondacks were towards the top of my list, and I had a long drive from Connecticut. Roughly 2.5 hours from Litchfield, my final destination for the evening was Lake George.

Situated on a deep-blue lake of the same name, Lake George is a year-round Adirondack getaway. The scenic drive towards northern New York offered beautiful views of the Catskill Mountains near the Hudson River and capital Albany. Once you pass the capital, it’s a straight-forward drive on I-87 North to Lake George.

Those Adirondack views shine overlooking the lake, and it’s a delightful place to relax for the evening. Whether you decide to book a Lake George cruise or lounge on Million Dollar Beach, you can’t go wrong at this lovely resort town. Just make sure to drive Prospect Mountain Highway before it gets dark for an unbelievable Lake George vista.



Day 6 – Adirondacks (NY)

Using Lake George as my base, I decided to spend another day in northern New York and the Adirondacks. With over 6 million acres of pristine wilderness, Adirondack Park is a nature lover’s paradise. Dozens of peaks soar over 4,000 feet, thousands of lakes create aquatic adventures, and more than 100 charming towns call this beautiful region home. You could spend a lifetime in the Adirondacks and hiking in New York, and you still won’t discover every inch of its natural beauty.

For my full day here, I ventured to several of the famous lakes sparkling beneath the massif. After checking off Lake George the previous day, it was off to more Adirondack wonders. My first stop was Lake Placid to explore the village that hosted the Winter Olympics twice. Mount Van Hoevenberg hosted many of the events, and snow-topped Whiteface Mountain sits high above the lake.

Just 10 miles from Lake Placid, Saranac Lake is another beauty where the foliage glistens on the water. My final stop was the freshwater Lake Champlain that sits on the New York-Vermont border. As one of America’s largest lakes, it’s a boating and kayaking paradise. There are several gorgeous state parks here, such as Cumberland Bay State Park and Niquette Bay State Park on the Vermont side.



Day 7 – Adirondacks (NY) to Green Mountains (VT)

Since Lake Champlain straddled Vermont, it made the perfect place to spend the night and start the following day. From its dazzling shores, I began my journey to the Green Mountains of Vermont. The mountain range runs north-south across the entire state, but I stuck to the northern side for my travels. Ultimately, the mountain resort town of Stowe was where I set my GPS.

Stowe is about 2-2.5 hours from Lake Champlain, and the route requires a ferry ride. The ferry offers stunning views of the lake and adjacent mountains for a magical crossing beside your car. At just over one hour long, the ferry was the perfect time to relax for a while. Vermont’s foliage is possibly New England’s best, and fall brings leaf peepers from across the globe. Its greenery shines during spring and summer, while the winter months host a snowy wonderland.

From this adorable town, there all tons of activities to have an exciting day. The nearby mountains entice hikers who love chasing waterfalls, and the area has many fantastic eateries. Just make sure you have plenty of energy if attempting to summit Mount Mansfield, Vermont’s tallest peak.



Day 8 – Green Mountains (VT)

Vermont’s scenery was indescribable, and I had to add another day here on my New England itinerary. One of my activities for the day was making the drive down the Green Mountain Byway. Between Stowe and Waterbury, this short journey packed tons of beautiful sights. You’ll pass pristine forests, farmlands, and quaint villages as you travel along the spine of the Green Mountains. With the mountains at your fingertips, the byway is a goldmine for outdoor recreation.

For nature lovers, pit stops at Smugglers’ Notch State Park, Moss Glenn Falls, or Little River State Park are my recommendations. Once you arrive in Waterbury, spend a couple of hours walking around the historic district. I’d also advise stopping by a farmers market to pack your bag for a relaxing picnic. Vermont’s nature is sublime and makes you never want to return to big city life.


Day 9 – Green Mountains (VT) to White Mountains (NH)

After peaceful days in Vermont’s Green Mountains, it was time to drive into New Hampshire to explore the White Mountains. I did much research on this fabled mountain range and its intense hiking trails. Fortunately, it’s a short 90-mile drive from Stowe to reach my White Mountain base. The scenic route crosses through small Vermont towns before entering New Hampshire. Turn onto Vermont Route 15 East and connect to U.S. Route 2 before heading down I-93 South to the White Mountains.

When the granite cliffs came into full view, I couldn’t contain my excitement to continue my adventures. As New England’s most rugged peaks, the White Mountains attract the hardiest hikers in the region. For any readers who love hiking, make sure to place an asterisk beside this spot on your New England itinerary. My final destination for the evening was Lincoln, and I made sure to rest up for some tiring days ahead.



Day 10 – White Mountains (NH)

Prepare to lace up your hiking boots in White Mountain National Forest. Many of New England’s tallest peaks and most challenging treks are in this scenic area of New Hampshire. The Appalachian Trail cuts through the White Mountains and gives AT thru-hikers some of their most intense days. There are so many incredible trails here beyond the Appalachian trail and you can easily find the best hikes in New Hampshire here. For your base location, I think Lincoln is your best bet when exploring the White Mountains. The picturesque town of Jackson is a worthy alternative to base yourself.

For thrill-seekers, summiting a New Hampshire peak should be towards the top of your New England bucket list. At the top of the list is Mount Washington, the tallest mountain in New England. Its summit stands at 6,288 feet, and the climb is among the most dangerous in America. If you’re brave enough to attempt this feat, make all the necessary preparations. Several people have tragically died trying to climb Mount Washington due to falls or severe weather.

While Mount Washington is the life-changing experience I recommend, there are many other awesome day hikes in New Hampshire. Another scenic area of New Hampshire is Franconia Notch State Park, and it has jaw-dropping mountain vistas.


Day 11 – White Mountains (NH)

New Hampshire was my favourite New England state for hiking, and I had to stay one more day. The rugged peaks of the White Mountains offer sweeping vistas, and I wanted to see more. Honestly, I could’ve spent weeks hiking the White Mountains, but two days was okay for my road trip.

My top-rated New Hampshire hike was the Mount Lafayette and Franconia Ridge Trail Loop. The 8.6-mile loop is one of the most challenging New England treks, and it’s only for veteran hikers. You’ll climb three rugged mountain peaks and eclipse 4,000 feet of elevation gain. But the rewarding view from the Mount Lafayette summit makes up for the brutal climb.

Mount Lafayette is the Franconia Ridge’s tallest peak, but it’s my favourite view anywhere in New Hampshire. If you’re eager to add the trek to your itinerary, you may want to camp near Mount Lafayette. Luckily, Lincoln is only 11 miles south and a quick drive from the base down I-93.



Day 12 – White Mountains (NH) to Acadia National Park (ME)

After pushing myself on a couple of daring New Hampshire hikes, it was time to venture to Maine. Situated on Mount Desert Island, Acadia National Park was my destination for this final stage of my adventure. One of America’s most visited national parks, Acadia has over three million visitors per year. With its untouched coastline, pristine beaches, and sparkling lakes, Maine rewards you with nonstop beauty.

Before reaching the Maine coast, I had to drive through the state’s rugged, mountainous interior. The best route from the White Mountains to the Atlantic coast is the 34.5-mile Kancamagus Highway. Otherwise known as New Hampshire Route 112, “The Kanc” is one of my favourite scenic New England drives. From my Lincoln base, I drove the route to the town of Conway. And I was speechless every second of the journey.

The Kanc offers sensational White Mountain views, cuts through enchanting forests, and passes cascading waterfalls. If you can’t get enough of New Hampshire’s incredible hikes, there are many trails and campgrounds here. Some sites I highly advise stopping at include Sabbaday Falls, Lower Falls, the Albany Covered Bridge, and the Rocky Gorge Scenic Area. Leaf peepers will adore this American Scenic Byway for its breathtaking fall foliage.

From Conway, the remainder of the drive to Mount Desert Island takes nearly four hours with no stops. After stopping at numerous scenic viewpoints on The Kanc, I wanted to reach Acadia National Park by nightfall. Bar Harbor was my resting spot for the evening as I rested up for an adventurous day exploring Acadia National Park.



Day 13 – Acadia National Park (ME)

When I organized my New England road trip itinerary, Acadia National Park topped my list of places to see. Its rugged coastline, sandy beaches, and epic hiking trails tapped into my adventurous spirit. Honestly, a road trip through Acadia National Park isn’t enough, and I could spend weeks exploring its awe-inspiring landscapes.

For the sake of this road trip, Park Loop Road is a must-do since it takes you to many of the park’s top natural wonders. After watching the sunrise at Cadillac Mountain, drive the 27-mile route to beloved sights such as Sand Beach or Thunder Hole. For daredevils reading this, the Precipice Trail is an adventure that’ll provide an adrenaline rush. To refuel for lunch, stop by the Jordan Pond Restaurant or have a picnic at Echo Lake.

After a packed day of thrills, my favourite spot to watch the sunset is at Bass Harbor Head Lighthouse. Watching the piercing orange and purple colours light the sky by the cliffside lighthouse is a magical sight. The cozy town of Bar Harbor serves as the gateway to Acadia National Park and is where I spent the evening. You’ll find boutique hotels, charming B&Bs, and other relaxing accommodations for a restful sleep.

In case you find yourself with some extra time on your hands or maybe the whale watching at Cape Cod gave you a teste for more, Bar Harbor also has great whale watching opportunities. There are lots of places for whale watching in Maine but Bar Harbor is where I would recommend you to head out from.


Day 14 – Acadia National Park (ME) to Boston (MA)

Acadia National Park was a thrilling destination to conclude my road trip, and it was time to head back to Boston. Logan International Airport is about 260 miles from Acadia, but the ride is spectacular. A portion of the route follows the wild Maine coast and makes you want to stop every few miles. You made find this hard to believe, but Maine has more coastline than California. With its rocky coast, sandy beaches, beautiful lighthouses, Maine’s 3,478 miles of coastline are a national treasure.

The bulk of your journey is along I-95 South, and you’ll have the chance to visit several adorable towns. U.S. Route 1 South is an alternative that’s slightly closer to the coast, but you’ll increase your drive time. My advice is to stick to the interstate unless you have plenty of hours to spare. The last thing you want is to rush to return your vehicle and catch a flight. If you’re itching to stop at some Maine coastal towns, Camden is the first one I’d suggest driving from Acadia National Park. Although you’ll need to take Route 1, it’s one spectacular town where the mountains meet the sea.

Just south of Portland, Old Orchard Beach is a classic stop for beach lovers in Maine. It’s a great stop on a summer road trip with a fun-filled boardwalk, sandy shores, and New England’s only beachfront amusement park. Kennebunkport is another quaint town with gorgeous cottages, stunning beaches, and a lively harbour. Other delightful stops before you exit Maine include Ogunquit, York, and Kittery.



Depart Logan International Airport

Your New England road trip comes to an end, and it’s time to return your vehicle to Boston. If you rented your car from downtown Boston, the rental agency might let you return it at the airport. My advice is to ask the agent beforehand if airport drop off is allowed and if there’s a fee. You’ll know in advance where you’re able to return the vehicle and plan your departure accordingly.


I hope you enjoyed this 14-day New England road trip itinerary. If you have any questions or recommendations, leave a comment below!

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I quit my job to travel in 2014 and it's one of the best decisions I've ever made. I know first hand how hard it can be to get everything in place in order to be able to travel, to know what to pack and where to go, let alone how best to go about your travels once on the road. Here I share everything I've learnt so far so you don't have to learn through as much "trial and error" as I did...Read more

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14- Day New England Road Trip Itinerary  14- Day New England Road Trip Itinerary  14- Day New England Road Trip Itinerary

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