Hey – do you want to go on a road trip? I think I speak not only for all native East Coasters like myself but for many travelers from all over the United States and the globe when I declare that the East Coast (of the United States) is awesome for many reasons. Best of all, it offers many incredible, memorable, and exciting opportunities for road trips.
As you surely know, the eastern part of our nation was developed and heavily populated early on in history. This was due to the vast number of settlers, immigrants, and enslaved people who arrived across the ocean from Europe and Africa between the fifteenth and nineteenth centuries.
As a result, this concentrated population on the East Coast has developed a rich history and deep-rooted culture. Connected by an extensive network of highways and roads, the villages, towns, and cities are complemented by inherent and varied natural beauty.
You can’t go wrong with an East Coast road trip. Whether you want to drive around New England, the mid-Atlantic states, or the South, you’re sure to figure out that there’s no better place for a road trip.
But… how do you decide where to go? We know that the people who know destinations best are people who travel, so we polled our readers on Facebook to narrow down the choices.
What We Cover
- TL;DR – Best Destination For…
- 1. Bar Harbor / Acadia National Park, Maine
- 2. Portland, Maine
- 3. Pinkham Notch & The White Mountains, New Hampshire
- 4. Cape Ann, Massachusetts
- 5. Salem, Massachusetts
- 6. Martha’s Vineyard, Massachusetts
- 7. Boston, Massachusetts
- 8. New York City, New York
- 9. Philadelphia, Pennsylvania
- 10. Williamsburg, Virginia
- 11. Charleston, South Carolina
- 12. Savannah, Georgia
- 13. St. Augustine, Florida
- What is the best time of year to visit these destinations?
- What are the most affordable destinations on this list?
- What other East Coast road trip are worth the drive?
TL;DR – Best Destination For…
|White Mountains, New Hampshire
|New York, New York
|National Park Fans
|Bar Harbor, Maine
|St. Augustine, Florida
1. Bar Harbor / Acadia National Park, Maine
Bahhh Haaahbor, so they say, in that often terribly imitated Maine accent, is super special. If you haven’t been there before, you absolutely must go.
Of course, most people visit Bar Harbor to visit Acadia National Park. You should do that, too, but the town of Bar Harbor is great on its own. It’s a cute little village with tons of shopping, great restaurants, and lots of gorgeous gardens.
Acadia National Park is spectacular. I’m enamored with the national parks of the United States, and there are so few on the East Coast. Acadia can compete with the best of the West, though, with its rocky shores, thick forests, mountain peaks, and incredible sunrises.
Bar Harbor and Acadia are quite a ways up the coast. It’s a three hour coastal drive from Portland, and in the summer, traffic backs up quite a bit in the small towns.
Keep this in mind, as even sometimes the very best road trips get a little frustrating en route. Once you get up to this part of Maine, all the time in the car will be worth it.
Things to Do in Bar Harbor:
Places to Stay in Bar Harbor:
2. Portland, Maine
Portland, Maine, is a great little city. I lived there briefly doing seasonal work, and although I was only there a few months, I felt right at home immediately.
The people in Portland are lovely and welcoming. The city is small and easy to get around and has more of a suburban feel than a city one. The waterfront and peak New England vibe sometimes makes you feel like you’re in a movie or novel.
These factors, plus a great food scene, proximity to natural beauty, and interesting maritime history, make Portland a super pleasant place to visit on a road trip almost any time of the year.
There’s just something special about Maine. Everyone who has been there will tell you that. From the rugged coastline of Acadia National Park described above to the high peaks of the northern Appalachians to lobster traps and fall foliage, Old Orchard Beach, Maine, has a character all its own.
And all of that comes together in Portland. Plus, the city is one of the best foodie cities in the country. Enjoy desserts and cocktails at Gross Confectionary, try lobster rolls at Eventide, and make time for brunch at Central Provisions.
Things to Do in Portland:
- Enjoy local cuisine on an Old Port culinary walking tour
- Take an evening kayak excursion in Casco Bay near the Portland Head Light
Places to Stay in Portland:
3. Pinkham Notch & The White Mountains, New Hampshire
New Hampshire is somehow still a little secret from many, but those in the know truly know that this part of New England is not only quiet, beautiful, and fantastic, but it’s well worth the effort to get up there. A road trip to this part of The Granite State may feel long, but you’ll experience and view incredible mountainous beauty.
Pinkham Notch is a mountain pass in these mountains. The notch itself is a U-shaped valley that is home to a number of rare or endemic ecosystems and is a hiker’s paradise. Mount Washington, the tallest mountain in the northeastern United States at 6,288′, borders Pinkham Notch to the west.
This area is an excellent destination for people who love nature and the outdoors. You’ll get plenty of both in northern New Hampshire.
Things to Do in the White Mountains:
- Paddle a kayak on serene Lake Tarleton
- Drive your car to the top of Mount Washington
Places to Stay in the White Mountains:
See Related: Best Hikes in New Hampshire to Try This Year
4. Cape Ann, Massachusetts
Everybody’s going to Cape Cod; it’s been that way for decades – no, centuries! Cape Cod is great and all, but people who are looking for a less-crowded road trip opportunity in Massachusetts might instead head to Cape Ann.
Where is Cape Ann, you ask? It’s the cape above the great Cape Cod – almost in New Hampshire. On it, you’ll find the towns of Rockport and Gloucester. On your road trip, you may find that you like both of them more than any of the popular towns on Cape Cod.
These are small towns. Gloucester has a population of about 29,000 people, and Rockport is only home to 7,000.
Both have every bit of that New England charm that you drove out this way looking for. You’ll love walking through their streets, smelling the salty air, and then going to dinner at a fresh seafood restaurant while you watch the sailboats go by. The word idyllic might as well have been coined seaside on Cape Ann.
Things to Do in Cape Ann:
- See whales up close and personal on a whale-watching boat tour
- Download and follow a scenic audio tour of Cape Ann
Places to Stay in Cape Ann:
5. Salem, Massachusetts
Salem is well known as the “witchiest city in the United States,” thanks to the fact that several women accused of being witches were put to death there in 1692. Although we know now that these women were innocent, the spooky reputation of this cool little town has persisted for hundreds of years.
You’ll find all sorts of interesting places to stay, stores, and museums within the city limits, along with some very cool century-old-or-more architecture. Salem has also been the setting for lots of movies and television shows, a fact that draws even more curious visitors.
Of course, your gut tells you to go there during the Halloween season, and you can, but maybe you shouldn’t. I went last year for a day trip in October, and the town was mobbed.
It was fun, but I was glad I wasn’t staying there – you had to wait in line to do anything. Any other time of year is better for a road trip to Salem.
You’ll find much easier parking and more affordable accommodations. Plus you’ll actually be able to shop and enjoy the museums.
Things to Do in Salem:
- Learn about the witch trials and local history on a self-guided walking tour
- Go on a haunted night tour with a local guide (here are some of our favorites!)
Places to Stay in Salem:
- Hampton Inn Salem
- Hawthorne Hotel
- Check into one of these other haunted Salem hotels!
- Check out more places to stay in the Salem area
See Related: Day Trips from Boston, Massachusetts
6. Martha’s Vineyard, Massachusetts
Martha’s Vineyard feels like it’s the playground of the rich and famous of the Northeast, and in many ways it is. That’s not all it is, however. It’s got such a lovely, welcoming, small hometown vibe with beautiful beaches, cutesy shops, and sublime outdoor dining in a breezy island setting.
You’ll love the beautiful Victorian homes and the heavy boat-focused culture throughout. There are lots of activities on Martha’s Vineyard, too – the island hosts a number of festivals each year, and there are lots of galleries and museums to explore as well.
Of course, you can’t road trip directly to Martha’s Vineyard – an island, after all – unless you drive some sort of James Bond-esque amphibious vehicle. Most of us have to take the ferry, which departs Woods Hole near Falmouth on the mainland.
It’s not cheap for cars, so you might want to leave your car there. We’ll say it still counts as a road trip if you drove to the ferry dock.
You’ll love your time on the island. Then, head back to your car to explore more of southeastern Massachusetts.
Things to Do in Martha’s Vineyard:
- Try a local scavenger hunt with your companions
- Go on a tour that covers all the island’s famous sights, including Oak Bluffs and Vineyard Haven
Places to Stay in Martha’s Vineyard:
7. Boston, Massachusetts
Boston is the biggest city in New England, and it’s rich with foundational American history. These factors alone make it an excellent choice for a road trip destination.
However, anyone will tell you that Boston is one of the worst cities in the nation for driving, so you may want to stay outside of Beantown and take the train daily to explore it. You’ll be glad that you did.
There’s plenty to do in Boston for every type of traveler. Take a tour of some local bars and breweries, or grab yourself a Boston CityPASS and hit up some top sites. You can’t go wrong.
Despite what you may have heard, Boston’s a family-friendly destination with fantastic child-centered attractions. Our favorites are the Boston Children’s Museum, the Museum of Science, and the New England Aquarium.
Other popular attractions, like the Museum of Fine Arts, Boston Common, the Boston Tea Party Ships and Museum, the USS Constitution, are all educational and interesting for all ages. Walk the Freedom Trail for a sampling of the city’s history.
Touring Boston is essential for first-timers. You’ll love listening to local accents and dining on lobster rolls and Boston baked beans, although maybe not in the same serving.
Overall, Boston is an all-American city, and every American should visit it at least once. After all, it’s one of the most interesting and pleasant cities on the East Coast.
Things to Do in Boston:
- Tour historic Fenway Park, our nation’s oldest MLB stadium
- Take a ride on the Boston Duck Tour and learn about the city from land and sea
Places to Stay in Boston:
- Residence Inn by Marriott Boston Harbor on Tudor Wharf
- The Colonnade Hotel
- Check out more places to stay in Boston
8. New York City, New York
Don’t get me started on New York. New York City is not only my favorite city in the United States, but it’s my favorite city in the world, and I feel honored and privileged to have called it my home for some years.
Everything about New York City is overwhelming, gigantic, and amazing. If I could afford to live there the way I’d like to, I’d do it in a heartbeat – for the rest of my life.
New York City is far easier to navigate by car than Boston, so be bold and don’t be afraid – having a car in New York City, even Manhattan, is not the end of the world. You can find parking if you’re patient or willing to pay.
However, as suggested for Boston above, you might consider parking outside the city and taking public transportation into the city daily. The New York City subway is easy and affordable to use and is, for the most part, safe. If you get lost, New Yorkers will help you – you may not believe me, but it’s true.
There are literally thousands of things to do in New York City. It has the best museums, restaurants, sporting events, parks, stores, bars, and music venues that you’ll find anywhere. Just go and dive in. New York City’s heartbeat will lead you to exactly where you need to be.
Things to Do in New York:
- Sample the best of NYC pizza on a West Village Pizza Walking Tour
- Take a comprehensive sightseeing tour with a group and a guide to check out all the popular sites you’ve always dreamed of seeing in person
Places to Stay in New York:
- Moxy New York City Lower East Side
- Best Western Plus Soho Hotel
- Check out the best places to stay in New York for sightseeing
- Check out the best places to stay in New York for families
9. Philadelphia, Pennsylvania
Philadelphia is another of my favorite cities in the nation and in the world. I lived there, too. In some ways, it’s a perfect combination of the two cities described above: Boston and New York.
It has the history, personality, and heart of Boston, paired with the grit, hustle, bustle, and attitude of New York. It’s a walkable city, and Philadelphians are the most interesting people you’ll ever meet.
Philly is another city where it’s easy to get around by car and to find parking. Just don’t move a lawn chair to take an open spot – that means that spot is saved by someone in the neighborhood.
Don’t be timid about parking in Philly – in some places, even the medians are fair game. Driving in Philadelphia is fairly easy, as long as you pay attention to GPS.
Philadelphia is full of lots of park space, well-funded museums, historical sites, enthusiastic sports teams and fans. It’s another fantastic foodie city, so you’ll want to try a cheesesteak and then some.
You’ll also love the dedication of local artists. There are beautiful murals everywhere you look – many sanctioned, many not – and they serve as a showcase of the Philly spirit.
Editor Note: As a born-and-raised Philadelphian, here’s the inside scoop. For Cheesesteaks, go to Dalessandro’s or John’s Roast Pork – or hop across the river and try Bourdain’s favorite at Donkey’s in Camden. Other must try foods: Roast pork at DiNic’s, donuts at Beilers, and a cannoli from Termini Bros – all of which can be found at Reading Terminal Market.
Things to Do in Philadelphia:
- Go on an Old City Historic Walking Tour and learn about this city’s rich history
- Visit and tour the creepy and spooky Eastern State Penitentiary
Places to Stay in Philadelphia:
10. Williamsburg, Virginia
Williamsburg, Virginia, allows visitors to step back into the past while having plenty of fun in the present. This small city of 15,000 residents was the capital of the Virginia Colony from 1699 to 1780.
It played an important part in the American Revolution. Because of this, many colonial buildings have been preserved, and you and your friends and family can learn much about the early days of our nation.
Colonial Williamsburg is a historic district and living history museum in the heart of town. You’ll be so impressed with the costumed actors who bring the place to life – chatting up Thomas Jefferson is a memorable experience.
In addition to Williamsburg’s dedication to history, you’ll also enjoy visiting museums, amusement parks, and shopping centers in the area. This road trip destination will be fun and educational for the whole family and will surely be a trip that you’ll always treasure and will never forget.
Things to Do in Williamsburg:
- Enjoy a guided food tour with tastings
- Try a spooky Williamsburg Ghosts, Witches, and Pirates Tour in the evening, led by lantern
Places to Stay in Williamsburg:
11. Charleston, South Carolina
Charleston is the Crown Jewel of the South. Even though Charleston has a difficult history when it comes to the United States slave trade, today, it is a beautiful and lively city that is worth a visit.
The weather is pleasant in Charleston most of the year, making it an excellent choice for a road trip in any season. History is the game’s name in Charleston, and you can visit Fort Sumter National Monument and countless house museums around town.
You can also spend your days or afternoons in museums like The Charleston Museum, the South Carolina Aquarium, and the Patriots Point Naval and Maritime Museum. Be sure to make time for a carriage ride.
When not touring the city, dining in Charleston is an adventure, and you’ll love trying new places throughout your stay. It’s hard to fit the best restaurants into one trip, so you’ll have to save some for next time!
Things to Do in Charleston:
- Try a history and architecture tour of this beautiful city
- Go on a dinner cruise of Charleston Harbor with live music
Places to Stay in Charleston:
- Francis Marion Hotel
- The Limited Hotel
- Check out more of our favorite hotels in Charleston
- Check out our favorite neighborhoods to stay in Charleston
See Related: Best Breweries in Charleston, South Carolina
12. Savannah, Georgia
I know I said that Charleston is the Crown Jewel of the South, right above this list entry, but some might argue that that award should go to Savannah, and I’d have a hard time debating them. This city is also beautiful, historic, and memorable.
What will stick with you about Savannah after you visit it is its many parks, its striking trees covered in Spanish moss, and its down-home, thick, humid, southern hospitality. It’s one of the most enchanting places to visit on the East Coast.
This southern city is a great road trip destination because it’s a bit off the beaten path, and half the road trip adventure is getting there. You might stop at Hilton Head Island in South Carolina on the way – it’s also a spot worth checking out.
When you get to Savannah, though, you know you can look forward to southern cuisine, an incredible historic district, intriguing museums of all kinds, a lively music scene, fountains, shops, bars, and a lively atmosphere. You’ll likely want to spend a few days exploring Savannah once you arrive, so make it a destination, not a waypoint.
Things to Do in Savannah:
- Explore the city on a hop-on, hop-off trolley tour
- Take a guided bike tour of the city’s historic district
Places to Stay in Savannah:
- The Marshall House, Historic Inns of Savannah Collection
- Hotel Indigo Savannah Historic District, an IHG Hotel
13. St. Augustine, Florida
St. Augustine, Florida, is on the northeastern coast of the Sunshine State and is widely believed to be the oldest continuously inhabited city in our country. It was first settled by the Spanish in 1565!
It’s unique as United States cities go because it’s full of Spanish colonial architecture, including the Castillo de San Marcos. Thi 17th-century Spanish fortress is open for visitors to tour.
In addition to the historical sites, visitors will also find beautiful beaches at St. Augustine Beach and Crescent Beach. Take time to watch wildlife at Anastasia State Park.
This city of about 15,000 residents is an excellent road trip destination – especially because you don’t have to travel too far into Florida to enjoy it. Still, if you are headed to other destinations in Florida, then St. Augustine is a great stopover option en route. You’ll really love this city and will find that it’s not like anywhere else you’ve been in the USA.
Things to Do in St. Augustine:
- Take a boat trip on a pirate ship to watch the sunset and enjoy the lights of St. Augustine.
- Try local cuisine on a wine, cocktail, and food tour of the city
Places to Stay in St. Augustine:
What is the best time of year to visit these destinations?
The best time for a road trip is always in the spring or the fall, especially for these East Coast road trip destinations. In the winter, you either have to fight with weather in the north, or fight with crowds in the south – and summer is too hot and humid everywhere.
What are the most affordable destinations on this list?
You can find affordable and budget accommodations in any city in the United States if you book far ahead and do your research, but some places will always be more expensive than others – Boston, New York, and Philadelphia in particular.
Some of the smaller towns on this list may still be expensive, though, depending on when you go. Still, you can always enjoy an affordable weekend in cities like Portland, Williamsburg, and Charleston.
What other East Coast road trip are worth the drive?
There are so many great places to visit on the East Coast! Driving the Blue Ridge Parkway, which runs for 469 miles through western Virginia and North Carolina, is something every road tripper should do at least once in a lifetime. Shenandoah National Park is along that route and is worth a stop or even a designated visit on its own – the Blue Ridge Mountains are truly spectacular.
Beyond that, you might consider a road trip to Everglades National Park in Florida or Congaree National Park in South Carolina, or take road trips to great southern east coast cities like Atlanta, Richmond, or Raleigh. There are so many great places to visit on the east side of the United States – and you should hit them all.