Maine & Massachusetts self drive holidays

The main reason to recommend a self drive holiday in America is the freedom to have a good old explore.
When my family started planning our USA road trip, we all made a list of experiences we’d like to have that we could tick off along the way. Close to the top of my list was trying the famous lobster rolls in Massachusetts, preferably from a roadside shack – the way they’re supposed to be eaten.

And, a few months later when we crossed the border from Connecticut, that was literally the first thing I did. I can’t honestly say whether they were the best lobster rolls I ate in New England, because I ate a lot of them. And crab rolls. And clam chowder. But they were definitely the most memorable, sat at a plastic table with paper napkins under a bottle of hot sauce, with the salty tang of the sea in the air, and noisy gulls picking through the shells out the back. Hi, I’m Rob, and I base many of my holiday decisions around eating. This is my confession.

For Monty Bampfield, senior USA specialist at our partners Audley Travel, the main reason to recommend a self drive holiday in America is freedom. “It’s having the freedom to reach areas of great natural beauty easily,” says Monty, “to visit smaller communities, and just have a good old explore.” 

Self drive holidays in Maine and Massachusetts are all about the freedom that the open road gives you, to go wherever the mood takes you. That sense of freedom is very apt, given that this is where the American Revolution first began in 1775, freeing the colonists from British rule and ‘taxation without representation’.

And there is another great freedom to be enjoyed here too – freedom from development, as demonstrated by protected areas such as the Rachel Carson National Wildlife Refuge, or the Kennebunkport Conservation Trust – both of which steward ecologically sensitive landscapes while keeping them open for visitors – our self drive holiday partners can recommend plenty of scenic walking routes.

Our guide to bespoke self drive tours in Maine and Massachusetts has more details…

Highlights of a Maine & Massachusetts self drive holiday

Acadia National Park

Acadia National Park boasts many sublime hiking and cycling trails, offering differing levels of challenge, and all easily accessible from car parks. Our partners can recommend plenty of excellent routes. The park is located mostly on Mount Desert Island, and travellers usually stay in Bar Harbor, where you can take a boat trip with a local lobster fisherman. There’s a free minivan service from Bar Harbor to various park locations, which helps minimise traffic and air pollution.


Several key events early in the American Revolution, which secured colonists’ independence from British rule, took place in Boston such as the Boston Tea Party, the Battle of Bunker Hill, and the beginning of Paul Revere’s midnight ride. Before collecting your hire car, one of the best things to do in Boston is to take a walk on the Freedom Trail, a four-kilometre city centre route that takes you around 16 historic locations relating to the revolution.

Cape Cod

This gorgeous Massachusetts peninsula’s peak season is between Memorial Day (last Monday in May) and Labor Day (first Monday in September). During June, July and August huge crowds descend on Cape Cod for sport fishing and beach going, so you’re much better off visiting during the off season if you can. Whale watching is popular here, with humpback, fin and sei whales among the species likely to be seen. Our partners can arrange responsible tours for you that ensure the boats keep a respectful distance from the whales, and don’t cause them stress.

Concord & Lexington

The skirmishes that took place in Lexington and Concord were the first armed conflicts of the American Revolutionary War (1775-1783). The expression ‘The shot heard around the world’ comes from Ralph Waldo Emerson’s Concord Hymn, which commemorates these early exchanges. As well as visiting the battlefields, in Concord you can also take a walk around Walden Pond, where Emerson’s friend Henry David Thoreau wrote his famous treatise, Walden, on self-reliance and simple living amid nature. You can visit a replica of Thoreau’s one-room cabin.

Nantucket & Martha’s Vineyard

These idyllic islands south of the Cape Cod peninsula swell with huge numbers of day-trippers during the summer months, drawn by warm weather and gorgeous beaches. It’s fun just to wander picturesque little towns, slurping ice cream and admiring the charming old wooden houses. There is a car ferry from Cape Cod, but it’s both expensive and unnecessary to have a car with you for a short stay on either of the islands.


Not to be confused with Portland, Oregon over in northwest America, Portland in Maine is one of the most renowned foodie destinations on the east coast. Whether your tastes lie towards high-end restaurants, takeaways from food trucks, coffee roasteries, smoothie bars, farmers’ markets, or microbreweries, your appetites will be well catered to. One of the best ways to get to know the food and drink scene here, and the people behind it, is with a guided tour from a local expert, which our partners can organise for you.

Rachel Carson National Wildlife Refuge

Named in honour of the biologist and author whose book Silent Spring was a landmark in environmental science and conservation, this protected landscape is just a short drive from the town of Kennebunkport, making it ideal for a few short nature walks. Do ensure you stick to the marked trails though, in case birds are nesting. The refuge was created to protect migratory bird habitats around Maine’s coastal estuaries, and its expanding boundaries prevent encroaching development.


This historic port city just north of Boston is notorious for the witch trials in the late 17th century when 19 people, mostly women, were hanged after false allegations of witchcraft were made against them. With several witch museums, opportunities to cast spells or have your photo dressed as a witch, and an art gallery located in a Satanic temple, it’s fair to say Salem has embraced the commercial upside of this murderous legacy. Naturally, it gets busy around Halloween, but if steaming cauldrons and broomsticks aren’t your thing, Salem also has rich maritime history and attractive coastal views.

Maine & Massachusetts self drive itinerary

Ten days to two weeks is ample time to see a great deal of Maine and Massachusetts. By embarking on a circular route you can take in many of the must-visit locations.

You could get your trip underway in Boston, the state capital of Massachusetts. Boston is home to the Red Sox baseball team at Fenway Park, and the prestigious Museum of Fine Arts, which holds a vast collection including works from the Dutch Golden Age, the French Impressionists, and a substantial range of Japanese art. History looms large in Boston too, as this is where the first sparks of the American Revolution were lit. You can learn about the Boston Tea Party in the harbour, and walk the Freedom Trail around the city centre, before picking up your hire car and continuing.

Two hours north through beautiful New England countryside brings you to the coastal town of Kennebunkport, on the Maine coast, after which you might work your way inland through New Hampshire to the White Mountains National Forest. Alternatively, you could continue up the coast to Bar Harbour, gateway to Acadia National Park. By now you should already have settled into a routine for getting into and out of your walking shoes!

Moving south, a 350km drive will bring you to Rhode Island, from where you can go west to the Cape Cod peninsula, a honeypot for tourists in summer with its pretty beaches, wooden houses and sunny weather. Boat trips to Nantucket or Martha’s Vineyard open up even more beaches as well as island communities. And from Provincetown on the northern tip of Cape Cod it’s just a two-hour loop back up to Boston.
Travel Team
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The way that a swan glides along a river is wonderfully graceful. Beneath the surface of the water, though, its feet are kicking frantically. A good self drive tour is very swan-like. You’ll have a fantastic time exploring Maine and Massachusetts, perhaps walking in Acadia National Park, catching a Red Sox game in Boston, or getting acquainted with the seafood. But before, and during, your trip, your dedicated tour organiser will put in the legwork to ensure that everything unfolds as smoothly as a fresh-tarmacked road. Your accommodation, car hire and many of your activities will be pre-booked so you can relax and enjoy the journey.

As well as a comprehensive pre-tour phone call to answer any lingering questions you may have, you’ll head off on your travels with a set of detailed route notes. These contain tips and advice based on our partners’ years of experience organising self drive tours in Maine and Massachusetts, and are kept up to date, as tour organisers regularly visit the New England region themselves. Everything from restaurant recommendations to lesser-known viewpoints, and which shop sells the best homemade ice cream in Cape Cod, will be at your fingertips. And for peace of mind, should you need support while you’re on the road, someone will always be available 24/7, just a phone call away.


As self drive tours are entirely tailor made you have a great deal of choice in where you stay, and the level of comfort you want from your hotel. The only limitation is that our partners will only book hotels that they are themselves familiar with, to ensure their suitability. But there is an enormous breadth of accommodation available across the USA, so this is rarely an issue.

Wherever possible you’ll be staying in smaller, locally owned properties, and especially those that involve themselves with community or environmental initiatives, so that you can be confident your stay is really doing some good. In Boston you might stay at a hotel that supports several local and global educational projects. And in Bar Harbor you could stay at a hotel that is a member of the Friends of Acadia organisation, supporting conservation efforts across the national park and surrounding communities.

“In New England, a lot of the bed-and-breakfasts know the Audley name, because we send so many people to them,” says Monty Bampfield. “The same goes for many of the farm shops in that region – they get a lot of visits from our self drive travellers through the recommendations in the literature we provide.”

Types of vehicle

Hire cars are priced according to size – specific models and makes cannot be guaranteed. Neither can electric vehicles yet, sadly, although it is worth enquiring. While America’s charging infrastructure is very good, most car hire companies currently only have a few EVs in their fleets, so in all likelihood you will be driving a petrol (gas) or diesel vehicle. Hopefully this will improve in years to come.

Given that a Maine and Massachusetts self drive holiday will often begin in Boston, it makes sense not to collect your hire car straightaway on arrival. Instead enjoy a few days of car-free sightseeing in a very walkable city that also has good public transport connections.

When to go

The best time for a self drive holiday in Maine and Massachusetts is either side of the busy summer season, as many of New England’s quaint coastal towns and resorts get super-busy during July and August.

Instead, come between September and early November for the glorious fall foliage, or in spring (April through to June), when local people in popular spots such as Cape Cod are still painting shop fronts and fixing up fishing boats ahead of the peak season, and have plenty of time to share a friendly chat. Late-spring and early-autumn tend to be warm but brisk in the mornings and evenings. Bring a light jacket or woollen jumper for cosy beachcombing and forest walks. I can vividly remember a peaceful but chilly stroll on an empty beach in Provincetown, on Cape Cod’s northern tip, in April.
Written by Rob Perkins
Photo credits: [Page banner: Mercedes Mehling] [Intro: Justin Bisson Beck] [Acadia National Park: Wei Zeng] [Nantucket & Martha’s Vineyard: MV Vacation] [Types of vehicle: xiangfei Meng]