Whether you live in Boston or just want to visit Beantown and leave the city for a trip, there are many great places to explore throughout New England.
From small towns in Massachusetts and neighboring states to mountains and national parks, ski slopes, multiple ferry crossings and breathtaking lakes, we have a complete list of car trips from Boston.
Let’s start with the shortest, in descending order of time. If you have at least a week, scroll to the end!
1. More information about the witch trials in Salem, Massachusetts
40 minutes from Boston (15 miles)
The historic customs house is part of the National Maritime Historic Monument of Salem.
Paul Brady photos/Shutterstock.com
Our first destination can hardly be described as a real road trip, just 15 miles from downtown Boston, but I thought I would activate it for those looking for a shortcut by car.
Salem is a historic city, founded in 1626, and was an excellent port in early American history.
Salem is best known as the site of the Salem witch trials, which took place in 1692 and 1693. Of the 200 suspects, 30 have been convicted of witchcraft and most have been executed.
If you haven’t read it, take a look at Arthur Miller’s Melting Pot, a famous book that draws subtle parallels between witchcraft and the anti-communist agenda of the 20th century.
The locals are very proud of their magic association – the magic museum is one of the most popular attractions in the city, the witches are represented on the vehicles of the local police and the sports teams of the local high school are known as witches.
Salem has more to offer than 17th century magic. Salem has 12 restored historic buildings and a copy of an 18th century sailing ship.
There’s also the Seven Gabled House, which dates back to 1668 and is one of the oldest wooden houses in North America, the former Salem Prison, the Peabody Essex Museum and the Federal Street District, where you can learn more about the city’s history.
2. Visit to Plymouth, Massachusetts, the oldest city in New England
50 minutes from Boston (41 miles)
You can stroll through the pilgrimage houses of the Plymouth Plantation Living History Museum.
Plymouth is less than an hour south of Boston – take Massachusetts Highway 3 south of the city.
Plymouth is known as the Native City of America, one of the oldest settlements in North America and the first in New England when it was founded in 1620 by settlers of the famous Mayflower ship. The name comes from the English city where the ship first sailed.
Considering the rich history of the city, many historical monuments and places are worth a visit. The Plymouth Plantation is a replica of the original colony from 1620 and the Mayflower II is a detailed reconstruction of the original Mayflower ship – it was built in England, crossed the Atlantic Ocean in 1957 and still makes frequent short trips across Cape Cod Bay.
Plymouth Rock must have been the place where the first pilgrims landed and settled, although the exact location is very controversial. However, there are many historic buildings in the area, many of which can be visited, including Jabez Howland House and Harlow Old Fort House.
A large National Ancestral Monument dedicated to the pilgrims and the Pilgrims’ Museum Room with artifacts from early settlers and local Indian tribes will complement your education on how America was first established.
3. Tour of the fishing village of Rockport, Massachusetts
55 minutes from Boston (39 miles)
The port of Rockport, Massachusetts, is ideal for filming.
You can do Rockport in one day from Boston or stop further up the coast in New Hampshire and Maine. It’s fun and early to leave Boston to get past morning traffic, and depending on whether you start at the Tobin Memorial Bridge or the I-93, both routes take about the same amount of time.
Since Rockport is a small fishing village, it can be difficult to find a parking space and you have to eat about a dollar an hour. You can park at the Blue Gate Meadows parking lot, which is free of charge.
From the parking lot it’s a 20 minute walk to the city or $1 per shuttle – if you’re two, you’ll probably pay the same, but you don’t have to bother finding a place.
The most famous attraction of Rockport is motif nr. 1. The building on the pier is known as the most painted building in America, which has been painted by local artists for over a decade. The original building exploded in 1978, but was almost immediately replaced by a copy.
Rockport has some great restaurants. The glacier, which looks like it’s still alive in the 50’s, is an absolute must, and you really have to stay to taste the local lobster on the Roy Moore Lobster.
Not far from Rockport, there’s a strange paper house. The whole house, including the walls, doors and most of the furniture inside, was made by a mechanical engineer from newspapers in 1922.
I don’t know exactly how long it will take, but it’s amazing to see, and it has running water, electricity, a stove and even a working fireplace!
4. Spend the day on a beach in the Hamptons, New Hampshire
55 minutes from Boston (46 miles)
Hampton Beach is a popular holiday destination an hour’s drive from Boston.
If you want to get away from it all and lie on the beach to listen to the waves, the huge Hamptons Beach is less than an hour’s drive from downtown Boston.
The water is very clean (although the North Atlantic Ocean is a bit cool!) and the sand is fine and relaxing. On the beach there are lifeguards and enough space to put down a towel and relax.
Parking can be a bit difficult and with good weather it can fill up quickly, especially on weekends. It is best to leave early and healthy and have breakfast in the Hamptons after parking. Don’t forget that you have to buy a ticket first and show it in the car.
The beach offers everything you need for a fun day out – a promenade, shops and restaurants and a playroom where you can entertain the children.
Be careful when choosing a spot in the sand – the tide is quite high and can take up most of the northern part of the beach when it arrives. Choose a place a little further away so you can stay for the day.
5. Walking in the historic streets of Providence, Rhode Island
at 1 hour from Boston (51 miles)
Providence is one of the oldest cities in the United States.
Providence is the capital of Rhode Island and one of the oldest in the United States, founded in 1636. A trip from Boston to the smallest states offers a combination of history, charm, and great food.
Unlike some other former coastal colonies, Providence was founded by exiles from the Gulf of Massachusetts who wanted to leave the Puritan way of life and find another way.
Providence is relatively easy to reach from Boston – take the I-93 from the city and continue south on the I-95 after the merger. You arrive in the center of Providence in a few blocks and follow the highway in an hour.
Most of the Providence’s old buildings, museums, bars and restaurants are located around the point where the Wunaskwatke and Moshassak flow into the Providence.
The Stephen Hopkins House of the RISD Art Museum, built in 1707, and the First Baptist Church in America are within a block of each other and you can walk between them on Benefit Street, which is famous for its history of providence, from 18th century federal buildings to America’s most famous Baptist Church.
6. Walking on the water in Ogunquita, Maine
1 hour 20 minutes from Boston (77 miles)
The fishing village of Perkins Cove is worth the trip to Ogunquivit, Maine.
Although Ogunquivit is in Maine, which means you have to go through Massachusetts and New Hampshire, the size of the New England states means you can get from Boston in less than 90 minutes. Take the I-95 from Boston and turn off at York – Ogunquivit is 7 miles off the coast.
Ogunquit is another seaside destination on our list, and it is no coincidence that the beach here often gets high marks in various national prizes.
Take your time and walk the Marginal Way, a walk along the waterfront that ends at Perkins Cove, a former fishing village.
Most of the boats in the harbour are fishing boats and lobster boats, and some offer excursions if you want to see with your own eyes how things are going.
Yes, there are several souvenir shops selling tourist items, but it is also a great place to taste the local catch of the day before lunch, and by catch of the day I mean lobster. They’re in Maine!
7. Excursion to historic mansions in Newport, Rhode Island
1 hour 30 minutes from Boston (72 miles)
Castle Hill Lighthouse may be small, but it is an absolute must for your Newport trip.
Newport is located directly on the southern tip of Rhode Island. If you’re driving from Boston, I suggest you avoid Providence and take Highway 24 instead. It may not be a big highway, but you get there 20 minutes faster.
Since I live in Great Britain, this part of New England has a lot of interesting place names – the early English (and Welsh) settlers around Narraganset Bay must have missed their home by mentioning their new colonies Warwick, Bristol, Exeter, Portsmouth, Swansea and Somerset, but I am retiring.
In case you’re wondering what Newport is, the two nicknames are World Sailing Capital and Summer Retreat Queen!
If you like sailing or just like to watch boats with a salty breeze on your face, Newport is definitely the place for you. The city is home to United States Naval College and a major naval station. The America’s Cup was played in Newport for over 50 years, until it was moved to different locations around the world in 1983.
Walking around Newport you will see a combination of classical architecture, large villas and estates and beautiful cliffs. You can visit one of the huge villas south of downtown Newport or take a walk along the Cliff Walk that starts at Easton Beach and passes several of these villas before returning to Bailey Beach.
8. Eating a lobster roll at Kennebunkport, Maine.
1 hour 35 minutes from Boston (90 miles)
In the quiet harbor of Kennebunkport, Maine, things are going a bit slower.
You may have heard that Kennebunkport is the summer home of former president George W. Bush, and there are several good reasons why you would like to spend a long summer weekend in this small village on the Maine coast.
The numbers 1, 2 and 3 are the reasons why food, drinks and ice cream come to Kennebunkport. I’m not talking about trendy restaurants and Michelin stars – lobster sandwiches are the order of the day at Kennebunkport.
Despite the fact that the clamshell has received a lot of media attention and has been reviewed by the same publications as the New York Times, there are equally good alternatives.
After a walk through the historic district of Kennebunkport you will stop later in the afternoon on the other side of the Kennebunkport River at the Kennebunkport Brewery or Old Vines Wine Bar.
For dessert, try one of the unique flavours of Rococo ice cream or choose a speciality from Maine cuisine – a piece of blueberry pie, which is served in most of the city’s restaurants.
9. Back in Old Ferchard Beach, Maine.
1 hour 45 minutes from Boston (102 miles)
The Old Garden Beach Pier is a timeless classic.
I know the coast of Maine, at the top of that list, with Kennebunkport and Ogunquit a few places higher and Portland nearby, seems to attract too much attention, but I think you’re looking for a car that leaves Boston and takes less than two hours in one direction, they’re all great options.
If you have enough time, you can easily combine them to make an epic leap along the coast to the Canadian border, but if you’re limited to a day or two and want to relax on a classic beach holiday, Old Orchard Beach will fully meet your expectations.
Don’t forget, it’s not a fantastic view of the first-class beach. I am talking about a nostalgic return to the beach holidays of yesteryear with a nice pier, a beach walk with arcades and fast food and 7 miles of beach.
A few kilometres from Sako you’ll find Funtown Splashtown USA, which has a particularly descriptive name – it’s a large water park where children will be happy while you relax with a drink of your choice.
Don’t forget that most shops, restaurants and events are open from Memorial Day to Labour Day. If you come in low season, you can still enjoy it and less people will come, but most places are closed.
10. Break in Portland, Maine
1 hour 50 minutes from Boston (112 miles)
The old port of Portland, Maine is filled with trendy bars and restaurants in historic brick buildings.
Portland, Maine, is a city that combines the charm of a small New England town with the excitement of the arts and food scene.
On I-95 it takes a few hours to pass the other three Maine destinations while on our list.
The Portland Head lighthouse is located near the city in Fort Williams Park. It is said to be the most photographed lighthouse in America, which is a true masterpiece, although the famous artist Edward Hopper chose the Lighthouse of the Two Lights, a few kilometres to the south, for his painting.
Once you arrive in Portland, park your car and walk around the Old Harbour, the historic centre of the city.
The Portland Museum of Art is a great place for art lovers, and the Old Harbour is also a place to sample the local lobster sandwiches – don’t forget that food here is served in a paper bag, not on white napkins, so don’t change!
11. Mount Monadnock walk
2 hours drive from Boston (80 miles)
The view from the top of Mount Monadnock is worth the climb.
Mount Monadnock is just outside New Hampshire and is one of the best options for weekend walks without having to walk too far.
It will cost you $5 to drive to Monadonock Park and park your car there. Don’t try to save money and park on the street – you’ll add overtime to your workday, just get on and off.
There are two main hiking trails leading to the mountain from the car park – White Point and White Cross, and the longer Red Trail if you want to spend more time on the mountain.
If you don’t walk much and you want an easier route, I’d go up and down the White Cross Road – it’s much less steep and easier to walk, but the result is much longer.
For those who feel more prepared, climb the White Dot Trail (it gets rocky and sometimes a bit steep) and then descend the White Cross Trail – descending the steep sections of the White Dot Trail is not an easy or very good route.
As soon as you rise above the forest, you begin to enjoy the view of the surrounding valleys. If you climb to the top (3,165 feet) and the weather is clear, you can look at Boston’s skyline – the absence of other large mountains in the area will help you enjoy the panoramic views.
12. Relaxation in Cape Cod and Provinestown, Massachusetts
to 2 hours 10 minutes from Boston (115 miles)
Cape Cod seems a lot further away than it is two hours drive from Boston.
Cape Cod is the perfect place for a beach holiday, not only in Boston but along the entire east coast. Only two hours drive separates you from everything it has to offer, so you may have to reconsider your plans for next weekend.
There are incredible beaches around Cape Cod, and the southern part of the peninsula is particularly popular – go to Hyannis and nearby Craigville Beach, where the bay is relatively quiet.
The national coast of Cape Cod, on the outskirts of the city, has surprisingly long stretches of ideal sandy beaches, but the water is cooler and coarser, and marine life, including sharks, is more common – helicopters often circle around to warn of white spots!
Make sure you drive from Cape Cod Bay to Provincial City. It’s an ideal seaside resort where you can enjoy a hearty brunch in the morning before visiting the Pilgrims’ Memorial where Mayflower pilgrims set foot in the New World for the first time.
For dinner, there’s more than just a great local lobster – go to P-town’s canteens and try some authentic New England shellfish or a fried cod.
13. Walking along the Appalachian Trail in the White Mountain National Forest, New Hampshire
to 2 hours 10 minutes from Boston (132 miles)
The Peabody River is one of the many rivers that flow through the White Mountains in New Hampshire.
White Mountain National Forest covers 1,200 square miles in northern New Hampshire and is one of the best places to get out of Boston and spend time outdoors.
White Mountain is the only national forest in Massachusetts, New Hampshire, Maine, Connecticut and Rhode Island. There is only one national park in these four states – Academia National Park, located off the coast of Maine (#22 below). So if you’re traveling from Boston, you don’t really have a choice.
Mount Washington is the highest mountain in the northeast of the United States and reaches an altitude of 1898 meters. There are dozens of hiking trails on and around the mountain, including the Appalachian Trail, which runs through the park.
But if you like driving, there’s a treat waiting for you. A road leads to the summit and offers breathtaking walks and views – everything you could wish for for a perfect road trip.
The fare is $31 per car per driver, plus $9 per passenger, which is a little more expensive, but it will be fun if you make it to the top. The lift is not for bullshit – the average gradient is 12% (which is a lot), but you get this sticker on the bumper of Mount Washington, which is included in the ticket price!
You will also get an audio guide for the ascent and another one for the descent on CD. If you don’t have a CD player (and even if you do), roll up the windows and enjoy the wind as you go up the hill!
Be careful when walking in the White Mountains, especially in winter or during storms. The American Forest Service says in public that some of the peaks here have the worst weather in America. Wind speeds can reach over 200 miles per hour and winters can be very cold, so be prepared!
14. Exploring the Green Mountain Forest in Vermont
to 2 hours 50 minutes from Boston (139 miles)
Breathtaking green mountains stretch along the length of Vermont.
The Green Mountains are located in the state of Vermont, and most of these mountains form the Green Mountains National Forest.
Unlike many other national forests, there are a number of friendly small towns throughout the forest reserve. Bennington, Manchester and Arlington deserve a stopover with historic buildings and a relaxed mountain atmosphere.
There are 3 ski areas in the Green Mountains – the most popular are Mount Snow, as they are closest to cities like Boston and New York, but Mount Stratton and Mount Bromley also deserve it.
In summer you can walk the most famous trails in the country, both the Appalachian Trail and the Long Trail, which runs through the park and divides the trail by 100 miles.
If you want to mix nature studies, visit Lincoln Family Home, the mansion where President Lincoln’s son lived, and the historic Old First Congregation Church in Manchester.
A little further south, near Bennington, you can visit the Monument of the Battle of Bennington, dedicated to the famous Battle of the American Revolution, which is over 300 feet high.
15. Skiing in Killington, Vermont
at 2 hours 50 minutes from Boston (159 miles)
Skiing in Killington, Vermont, has picturesque slopes through a spruce forest.
Killington is the largest ski area in the east of the United States, with 155 ski runs covering more than 1,500 hectares and 21 lifts to go up the mountain.
From Boston, take the I-93 to Concord and then the I-89 to Lebanon, which lies on the White River, which also forms the border between New Hampshire and Vermont. If you cross the river, Highway 4 goes into the mountains and leads to Killington.
For those who don’t like skiing or snowboarding, Killington offers all the other snow-related activities you can imagine. You can go cross-country skiing, tobogganing, snowshoeing, ice skating and even a giant sled pulled by a snowmobile.
For skiers and snowboarders, Killington has so much to offer that it is the most visited ski resort in New England. Many slopes and sections are designed for experienced skiers – there are 5 snow parks with different jumps, a large half-pipe and complex routes, including the double black diamond Outer Limits.
But even the newcomers will have had enough. The Snowy Mountain is a large open slope designed exclusively for beginners. The ski area has other comfortable slopes for beginners and a ski school.
16. Iceland Block, Rhode Island
to 3 hours drive from Boston (101 miles)
The southeastern lighthouse is one of the attractions that will take you around Block Island.
Block Island is a small island off the coast of Rhode Island and about halfway between Rhode Island and Montauk on Long Island.
To get from Boston, you have to drive to Point Judith, Rhode Island – the route goes through Providence and should take an hour and a half in friendly traffic.
The standard ferry sails all year round and costs just under $25 per person for the return flight, which takes 55 minutes to reach the island. If you want to take the car with you, it costs $80 extra (or almost $100 for a larger car). Standard ferry services are every two hours in summer and only a few times a day in winter. Check the calendar on the Block Island Ferry website.
If you want to save time, there are faster boats that cost just under $40 and only take 30 minutes to get to Block Island, but they only sail during the summer season and have no vehicles with them.
It’s easy to spend time on Block Island – the atmosphere is really relaxed and all the beaches around the island are public and free. Yes – even when parking!
There are curious neighbourhood shops, great restaurants to visit and above all the opportunity to distract your thoughts and have a good time.
17. Driving on Winter Road to Stow, Vermont
at 3 hours 15 minutes from Boston (199 miles)
The Stowe in Vermont is a great place to visit at any time of year, but it is especially beautiful in autumn.
Stow is another very popular ski resort in Vermont, and although it is smaller than Killington (#15 above), it is often less crowded because of the extra time it takes to get there and can be a good option for a weekend drive from Boston.
Stow Mountain Ski Resort is located a few kilometres from the town on the mountain road (Highway 108), with a ski area divided on both sides of the valley between Mt. Mansfield and Spruce Peak.
Although there are only 12 lifts, most of them are chairlifts and a fast gondola lift to Cliff House, making the climb more relaxed.
The historic town of Stowe, far from the ski slopes, is also worth spending some time here. The classic buildings, dressed in wooden clothing, have beautiful local shops and restaurants that enhance this charm. The choice of hotels in Stowe is excellent – there are some very good luxury options, but the average standard is also very high.
The Smugglers Night is only 15 minutes away by car and has its own small ski area. If you want to go skiing with little money, this is a reasonable option, but if you can afford a Stowe, be sure to do it because the town, resort and skiing are much better.
18. Walking around Lake George, New York
at 3 hours 30 minutes from Boston (226 miles)
Lake George, in the upper part of the state of New York, is surrounded by forested mountains.
Colin D. Yang/Shutterstock.com
Lake George in the state of New York is the perfect place to relax, surrounded by tree-covered hills.
The shorter, more direct route through the Green Mountains of New Hampshire may be a little more picturesque, but it takes an hour longer than the I-90 to reach Albany, and then north via Saratoga Springs to Lake George.
Lake George was formed at the beginning of the 20th century. At the end of the 19th century it became a popular destination for New York millionaires because it could be reached directly by train from the Big Apple.
Today you can understand why they loved this place so much – the best way to see the landscape around the lake is to take a steamer ride. Please note that cruises are only held during the summer months, from May to October, and that October can only be at its best for the beautiful autumn leaves.
There are many footpaths on either side of the lake, although the East Coast offers the best choice and many great views – the Black Mountain Trail offers great lake views and is relatively easy to hike, and the Sleeping Beauty Mountain Trail is phenomenal although you will need to come early to beat the crowds and get a parking space.
19. Lake Champlaign and Burlington, Vermont
at 3 hours 30 minutes from Boston (226 miles)
Burlington is a beautiful town on Lake Champlain in the north of Vermont.
If the perfect place for a road trip is a place where you can do nothing for a few days or a week, then Lake Champlain in the north of Vermont is the perfect place for a road trip.
Follow the I-93 from Boston to Concord, then the I-89, which will take you to Burlington – an easy route for such a long journey.
The city of Burlington is a great place to live – around Church Street is a picturesque historic city centre with cobbled streets and buildings that tell the story of the city founded in 1783.
Burlington and its southern neighbour, Burlington, together have just over 60,000 inhabitants, but that’s enough to make this great city of Vermont almost four times the size of Rutland, which is the second largest city. Yes – Vermont is not very populated!
The city and the lake district are absolutely perfect for taking life alone and not doing much. Wake up late, have a quiet breakfast, take a boat trip and try a homemade beer at Foam Brewers for dinner. Rinse and repeat, no matter how long you stay.
20. New York, New York
4 hour drive from Boston (215 miles)
I think it’s impossible to get tired of New York’s breathtaking skyline.
The Big Apple may be a 4 hour drive from Boston, but if you’re in the city after a long break, New York is the obvious choice for a road trip.
You can get there by train, but it takes 4 hours, and you have to add up the time it takes to get to the station and back from both sides. I may be a little biased when it comes to travel, but if you go by car, you see a lot more, and have the advantage of seeing places near New York City.
There are many reasons to visit New York – here are a few: Empire State Building, Statue of Liberty, Central Park, Times Square, Metro Museum, Brooklyn Bridge Walk, interior views of Grand Central Terminal and views of the skyscrapers at the top of the cliff.
If that’s not enough to get you excited, you’ve got incredible places to explore, far from the hustle and bustle of Manhattan – from Greenpoint to Brighton Beach, Brooklyn offers an incredibly diverse mix of people and cultures, and you haven’t seen New York City if you haven’t been to the Bronx.
If you want a good trip, return to Long Island and explore the vineyards and famous informal lifestyle before taking the ferry across Long Island Sound. See no. 23 below for more details.
21. Travel to Nantucket and Vineyard Islands from. Mars
to 4 hours drive from Boston (100 miles)
Nantucket’s quirky streets and historic houses make you feel like you’re travelling back in time.
Nantucket and Martha Vineyard are two islands off the south coast of Massachusetts. You can visit them, but the ferries come and go only from the mainland, so you have to go back before you can reach the next island.
Martha’s vineyard is closer to them, just 45 minutes by ferry from Woodshall. Many recommend parking the car and taking the ferry on foot – tickets cost $17 per adult for the return flight.
The problem is that, on the other hand, you’re either stuck in public transportation to get around the island, which is not the best use of your time, or you can rent a moped for most of the $100 a day and feel the adrenaline rushing every time a big truck passes on a narrow road.
If you want to do the right thing, book a car on a boat (you really should book in advance as they are for sale) – it will cost you $180 if you drive from Friday to Sunday for the return trip, but you can enjoy a few more days at Martha’s Vineyard. Make no mistake: if you want to save money, there are decent buses that take you, so it’s a matter of how much you care about comfort.
Barack Obama was famous for playing golf in Martha’s Vineyard, and in December 2019 the Obama’s bought a villa on the island for the modest sum of $12 million.
Nantucket is further away and more expensive, but Nantucket is really old school in New England. If you want to stroll through the picturesque streets of the old town, you will need a ferry from Hyannis.
When you’re in Nantucket, it’s best to leave your car on the beach. It’ll cost you $500 if you send them to Nantucket and send them back over the weekend. The island is small enough to visit during the day and you don’t need a car to drive around it.
Ferry tickets cost $37 per adult and the ferry takes 2 hours and 15 minutes to get there, or you can pay about twice as much and board a faster Hy-Line ship that will get you there in an hour.
22. Discover the beauty of Akadia National Park, Maine
at 4 o’clock 40 minutes from Boston (280 miles)
The rocky coastline of Acadia National Park is truly breathtaking.
Acadia National Park may be the only national park in New England, but it is perhaps one of the most spectacular, if not the most spectacular, in the country, and it’s worth it.
I couldn’t stop to take a picture for Akadia, so I recorded Jordan’s Pond – 2 still seems like a small number to show how great nature and scenery is here, but we have to do it.
The landscape around the Jordanian pond leaves you speechless.
Akadia National Park lends itself just as well to outdoor walks as any other part of the country. There are rolling forests, beautiful lakes and sounds, rocky coasts, many hiking trails and small towns and decent restaurants in places you might want to stay for lunch!
The fastest way to get there is via the I-95/I-295 road to Bangor, then the 1A road to Akadia.
But real car journeys are not about speed, so leave the highway at Portland or Freeport and take Highway 1 instead. You pass through countless beautiful coastal towns, eat more lobster than you thought and see dozens of beautiful lighthouses in exchange for a 40 minute drive.
You can also find accommodation for one or two nights on the road to interrupt your trip or even add Portland to your itinerary, making the idea even better.
23. Long Island and Montauk Winery
5 hours from Boston (196 miles)
The Montauk lighthouse is located at the eastern end of Long Island.
Long Island, New York, is an incredible distance from Boston, and it’s easier to get there than you think.
The journey from Boston to New London, Connecticut takes about 2 hours, and you must take a ferry to Long Island. The ferries take an hour and 20 minutes to arrive on Long Island in less than 4 hours, despite available waiting and embarkation times!
Check your schedule and book your tickets in advance. The usual price per day is $61 per car and driver for a one-way trip (which seems a lot compared to Nantucket and Martha’s wineries).
If you have registered online on the Cross Sound Ferry website and paid in advance, you can cross the ferry for less than half the price. So take 5 minutes of your time and reserve a seat.
You arrive on Long Island directly at North Fork, where most of the island’s best vineyards are located. Bingo!
Take the time to get out and visit/stop at a few towns and vineyards along the way. You may have never heard of wine-growing on Long Island, but you will probably be pleasantly surprised by what you taste. I discovered Long Island wines when I lived in New York, and I’m still a big fan.
After a walk through the famous Hamptons, where the richest in New York have their second home, go straight to the top of Long Island and visit Montauk.
This sleepy town is perfect for a day or two to put your feet up and watch the waves, although it has become much more popular with visitors since The Affair’s Showtime broadcast and most of them have settled here.
24. A study of the history of the nation in Philadelphia, Pennsylvania
to 5 hours and 10 minutes from Boston (321 miles)
Philadelphia Independence Hall is one of the most important historical places in the country.
If you want to combine a great city tour with an introduction to American history, where much of it happened, the maps should show a road trip from Boston to Philadelphia.
It’s a long drive from Boston – first to New York, then south to Philadelphia. Whether you decide to bypass New York City and cross the Hudson River via the Governor Mario M. Cuomo Bridge or via George Washington, it will take about the same amount of time, so choose the route that works for you.
You can spend a few days in Philadelphia or stay longer – the more time you have, the more you’ll get to know this great place and see some of the most amazing sites.
The Independence Hall, with its historical significance and a copy of the Declaration of Independence, is an absolute must. After visiting the building where independence was declared and where the constitution was adopted 11 years later, you can stop by the Liberty Bell, City Hall and the Society Hill Historic District, which are part of the Independence National Historic Park.
Don’t forget to have lunch at the Market Reading Terminal – these stalls sell everything from jams to barbecues and desserts, and it really is a Philadelphia experience.
Don’t miss the art museums – Philadelphia has some of the best museums in the country, and the Philadelphia Museum of Art has those famous steps where the cult film Sylvester Stallone the Rocky played.
25. Full cycle around Lake Ontario
9 hours from Boston to Toronto (550 miles)
Tranquil water from Lake Ontario in Mississauga, near Toronto.
Michael J. Eves/Shutterstock.com.
This list wouldn’t be complete without the crazy option (and I usually take several!), so here’s a road trip for those who are two weeks or more old.
Start driving west of Boston in the direction of Oswego, which is on Lake Ontario. The trip along the I-90 through Albany and Syracuse takes 5 to 6 hours and can easily be completed in one day with breaks and lunches.
Oswego is a nice town where it is nice to eat after a long journey.
From Oswego this route turns clockwise around the lake so you can see much of upstate New York before reaching Niagara Falls and the beautiful lakeside town of Niagara after crossing the border with Canada (bring your passport and car papers).
Stop in Toronto and continue around the lake to the vineyards of Prince Edward Island before reaching Thousand Island National Park.
On the way back you can explore the incredible wildlife of upstate New York via High Peaks, Five Ponds, Sargent Pond and Dix Mountain on Lake George Road (see #18 above), or you can take the longer route through Ottawa and Montreal and drive back to the United States at Alburg-Noyan Junction to reach Lake Champlain in Vermont (#19 above).