Boston to Maine Road Trip: Your Complete Itinerary Guide

Boston to Maine Road Trip

America is hallowed ground when it comes to road trips. Ever since Kerouac published On the Road, the thought of driving around this amazing country has been on everyone’s minds. Whether you want to explore Hawaiian islands or drive from coast to coast, there are endless wonders to be discovered. One option you might be considering is a Boston to Maine road trip.

This is a relatively short trip but also among the most epic. America’s northeastern coast holds spectacular beauty that can be enjoyed at any time of year. Before you set off, though, it’s important to do your research. Make sure you know what to expect, what to pack, how long you need, and where to stop.

This article will help you make your Boston to Maine road trip as epic as possible. Keep reading to increase your understanding of this region. Learn how to prepare for an epic road trip in America’s northeastern states.

Why Take a Boston to Maine Road Trip?

Boston skyline
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The Great American Road Trip is hallowed ground for the traveler. It’s the ultimate expression of freedom and exploration. America is a vast patch of land that requires time to fully understand. That’s why many people choose to rent or buy a car and then journey across different parts of the country. Rather than staying in a single destination, you can get to know this land better by taking to the road.

The question is, which route do you take? Route 66 is perhaps the most famous but at almost 2500 miles (almost 4000 km) in length, this isn’t feasible for most people. Instead, it’s better to choose a shorter route that can be accomplished more quickly. A Boston to Maine road trip is closer to 250 miles, making it doable in a single day. If you’re pushed for time, then this is the perfect way to get all the benefits of a road trip, without spending a lot of money or taking loads of time off work.

Different parts of America offer different benefits for tourists. Yellowstone National Park might be the most beautiful area of the country while southern states might contain more fascinating indigenous history. If you’re into the founding of this great nation, though, then it all begins in the northeast. That’s where Europeans first arrived to found the USA as we know it today. A Boston to Maine road trip is the best way to discover the history of America while traveling through stunning scenery.

How Far is a Boston to Maine Road Trip?

Boston at night
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Every road trip will be unique, meaning that the distance you travel will vary. It will vary depending on which part of Boston you start from, where specifically in Maine you end up, which route you take, which sights you want to see, and how far you deviate from the original route. This can drastically alter the total journey time of your trip.

If your plan is to leave central Boston and drive directly to a town in central Maine like Guilford, then your road trip will be a little under 250 miles (400 km). However, most road trippers won’t take such a direct route. Road trips aren’t about getting to a place as quickly as possible. They’re about experiencing and enjoying the journey along the way. They’re about unexpected obstacles and spontaneous detours.

Therefore, it’s best to assume your route will be longer than this. Sit down with a map (either physical or online) and plot the route you want to take. This is the easiest way to see how long the distance really is. The chances are that your total driving journey will be more like 300 to 400 miles (480 – 640 km) long. You’ll then want to add a bit on to account for detours you make along the way.

How Long Does this Road Trip Take?

Boston roads
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Like the distance, the time it takes you to complete this journey depends on a number of factors. If you wanted to, you could easily complete the journey in under half a day. After all, the journey time between Boston and Guilford, Maine, is under four hours. You could easily do it in one sitting, without taking any breaks. But what kind of a road trip would that be?

Most people who make this journey want to take their time. They want to stop at beauty spots and historical monuments. They want to get out of the car every now and then to explore this fantastic bit of land. Perhaps you want to stop to eat. Also, you’ll be unlikely to take the quickest route between the start and the end of your Boston to Maine road trip.

Once you’ve added in detours and stoppages, this road trip is likely to take longer than a day. We recommend staying overnight at least once along the way, turning this into a two-day drive, perhaps over the weekend. However, it’s impossible to know exactly how long your journey will take. The point of road trips is that they’re spontaneous and you decide when to stop and when to drive as you go, based on a gut feeling. You’ll only know how long this trip will take once it’s done.

Key Stops to Make

Boston public garden
Photo by Envato Elements

In order to plan your trip, you need to decide exactly where to stop along the way. These are the key sights that make the trip worth taking. Fortunately, there is plenty to experience along the route from Boston to Maine. The important thing is to decide whether you want to visit natural beauty spots, historical monuments, big cities, or a mixture of all three.

Once you leave Boston, the main urban areas of interest include Newbury Port, Salisbury, Hampton, Portsmouth, York, Portland, Brunswick, and Waterville. There are even more towns further north, depending on how far into Maine you travel. As the names of the towns imply, these were founded by the English as soon as they arrived in the New World. That makes them excellent places to learn about the founding of America.

In terms of natural beauty, you’ll want to stay near the coast for glimpses across the great Atlantic Ocean. The biggest and most beautiful national reserves include Wells National Estuarine Research Reserve and Rachel Carson National Wildlife Refuge. Both of these places are must-visits if you love nature. In terms of monuments, lookout for historical homes, lighthouses, and observatories along the way.

Road Trip Packing Guide

couple on road trip
Photo by Envato Elements

The Boston to Maine road trip involves traveling through some of America’s coldest destinations so be prepared for this. If you’re from the south, then you probably don’t realize just how cold it can get up there. In Boston – the southernmost point on this road trip – winter temperatures can drop as low as 40°F (-5°C). In this case, you’ll obviously need warm clothes to keep you warm throughout the trip.

Furthermore, the cold brings snow, which you need to be prepared for. Ensure your car is fitted with snow tires and always carry a shovel to dig yourself out of trouble. You should also make sure that your car is always fully stocked with plenty of food and water so you know you’ll be okay if you get stuck.

Of course, you could always make the trip during the summer. In this case, it’ll be much less dangerous and you won’t need to pack so much survival gear. The good thing about this trip – compared to, say, an Arizona desert road trip – is that you’ll never be too far from a town. That means you can pack light and always buy more gear if you need it.

Things to Do When You Get to Maine

Boston cityscape
Photo by Envato Elements

Your Boston to Maine road trip doesn’t need to end once you reach your final destination. If you’re going to Maine anyway, make sure you have a list of things to do once you get there. This is the perfect chance to round off your trip and end it on a high. With that in mind, research the best things to do in Maine. You can pick your favorite to be your final destination.

What are your favorite things to do? Love American food? Eat in Maine’s best restaurants. Prefer culture? Visit all the museums. This is your unique itinerary so it’s up to you to do the research and plan the best adventure. However, to get your creative juices flowing here are some of the best things to do in Maine:

  • Explore Acadia National Park
  • Take a trip out to Monhegan Island
  • Marvel at the Victoria Mansion in Portland
  • Wander through the Portland Museum of Art
  • Learn history at the Maine Maritime Museum
  • Have a look around the Nubble Lighthouse
  • Relax on Old Orchard Beach

Maine is full of incredible beauty and fascinating history. A road trip gives you the freedom to explore it at your own pace, prioritizing the things that excite you the most. Make sure you choose something to end your Boston to Maine road trip and use it as motivation to keep on chewing up the miles.


For more than 11 years, Joe has worked as a freelance travel writer. His writing and explorations have brought him to various locations, including the colonial towns of Mexico, the bustling chowks of Mumbai, and the majestic Southern Alps of New Zealand. When he's not crafting his next epic blog post on the top Greek islands or French ski resorts, he can often be found engaging in his top two hobbies of surfing and hiking.

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