5 Great Road Trips from Boston

The far northeast of the United States is known as New England, a name given to the region by English colonists in the 17th century because the rolling hills reminded them of home. The largest city is Boston, which is also the capital of the state of Massachusetts. Although not as large as Central Park in New York, Boston also has a park—actually, two: Boston Common and the Public Garden —around which the heart of the city is centered.

The North End used to be a peninsula, and this is where the city’s origins lie, with beautiful historic buildings, including the oldest one, the Paul Revere House, dating from 1680, and the Old North Church. These two buildings played an important role in the colonies’ rebellion against the mother country, Great Britain. They are located along the so-called Freedom Trail, a unique collection of museums, churches, cemeteries, parks, a ship, and other historic sites that tell the story of the American Revolution and its aftermath. Today, the oldest part of Boston is known as Little Italy, with Italian restaurants, coffeehouses, pastry shops, and old-fashioned delis.

In the South End, you’ll find buildings of a slightly more recent date. The historic district is the largest remaining contiguous Victorian-era neighborhood in the U.S. The chic Beacon Hill neighborhood, north of the central city park, also features Victorian houses illuminated by antique lanterns. An iconic little street here is Acorn Street.

Boston is a fantastic city to spend a few days in and a great base for road trips in a rental car. The historic sights outside the city are just as interesting as those along the Freedom Trail. But it’s not just about history: in Massachusetts and neighboring states, you’ll find rugged coastlines, beautiful beaches, picturesque colonial architecture, stunning natural areas, and, of course, the world-famous New England landscape. We’ve mapped out five of the best routes here, including some along so-called scenic byways. You can rent a car right upon arrival at the Boston airport or in the city itself.

1. Cape Cod

If you’re in Boston during the summer months, a trip to Cape Cod is practically a must. It’s a long, narrow, and curved peninsula that juts out into the Atlantic Ocean and is often compared to a bent arm. Cape Cod is famous for its charming coastal towns, beautiful beaches, and fresh seafood. To get the most out of this road trip, drive your rental car along Route 6A—also known as Old King’s Highway—through historic towns like Sandwich, Barnstable, Brewster, and Orleans. At the very tip lies Provincetown, an artists’ colony and the heart of LGBT life on The Cape, as the peninsula is commonly called.

There’s a beautiful bike route to Provincetown called the Cape Cod Rail Trail. Along this route, there are several spots (trailheads) where you can park your rental car and continue on by bike. You’ll then ride through the Cape Cod National Seashore, a protected nature reserve, where—in addition to biking—you can swim, paddle, kayak, hike, go birdwatching, or participate in a ranger program. Along the Cape Cod coast, you have a good chance of spotting whales (humpbacks), especially between mid-April and mid-October. There are also several seal colonies.

If you plan to drive to Cape Cod in your rental car during the summer months, avoid doing so on Friday evenings. Many residents of Boston and other cities have the same idea, so the roads leading to the peninsula get very crowded at that time.

Martha’s Vineyard / Nantucket

Ferries depart from the ports of Woods Hole, Falmouth, and Hyannis to Martha’s Vineyard, located south of Cape Cod. The island is a favorite vacation destination, boasting spectacular beaches and miles of hiking and biking trails. It’s no wonder that many celebrities have vacation homes there. If you want to take your car on the ferry, check with the local rental company when you pick up your rental car to see if they allow it. Note that for Martha’s Vineyard, this is only possible on the ferry from Woods Hole. Be sure to reserve a spot on that ferry well in advance online.

The island of Nantucket is smaller and lies farther from the Cape. In addition to its beaches, the island has a history as a center of the whaling industry. Whaling brought in so much money that large houses could be built. Nantucket Town, with its cobblestone streets and 18th- and 19th-century buildings, is designated in its entirety as a National Historic Landmark District. Ferries to Nantucket depart from Hyannis (car ferry) and Harwich (passenger ferries, operating only during the summer months). Additionally, during the high season, a ferry also runs between Martha’s Vineyard and Nantucket.

2. Essex Coastal Scenic Byway

North of Boston lies an area known as the North Shore, through which runs a beautiful road: the Essex Coastal Scenic Byway. This road, over 140 kilometers long, connects fourteen coastal towns, and along the way you’ll pass many sandy beaches, vast marshes, and historic landmarks. There are countless opportunities to park your rental car and follow a hiking or biking trail. Of course, you can also head out onto the water with kayaks or surfboards in one of the many coastal towns. As you drive out of Boston in your rental car, you’ll immediately pass a wide sandy beach, Revere Beach. The tranquility is sometimes disrupted by airplanes landing at Boston Logan Airport. In July, large sand sculptures are on display during the Sand Sculpting Festival.

Salem

The first major city along this scenic byway is Salem, which grew wealthy through overseas trade shortly after the Revolutionary War. Warships were converted for trade with the mysterious East, including China. Imports of pepper, silk, and other luxury goods of the time yielded enormous profits. You can still see that wealth in the historic parts of the city, such as around Chestnut Street. The Peabody Essex Museum houses a vast collection of Asian art, and a traditional Chinese house was even transported here and rebuilt in the museum’s garden. In 1692, the Salem witch trials took place—one of the most notorious cases of mass hysteria—during which more than 200 people were accused of witchcraft. The city long tried to sweep this painful history under the rug, but when that failed, it made a virtue of necessity. Salem now proudly bills itself as “Witch City,” and nowhere is Halloween celebrated as exuberantly as here.

Gloucester

From Salem, it’s just over a half-hour drive by rental car to Gloucester, the oldest American fishing port. The city takes pride in this heritage, as evidenced by the statue of a fisherman at the helm commemorating sailors who never returned, and Maritime Gloucester, a restored section of the old harbor. You can set out to sea on historic sailing ships, and there are also boat tours for whale watching. You might spot humpback whales, North Atlantic right whales, (blue) fin whales, sperm whales, and pilot whales, among others.

Before you reach Gloucester, you’ll drive past a medieval castle. Huh, don’t those exist in America? That’s right—this castle was built over a hundred years ago by the inventor John Hammond. Americans love this kind of replica, while Europeans, who are used to real old castles, are a bit less enthusiastic.

Rockport

As you drive to Rockport, you’ll pass one beach after another, so don’t hesitate to head toward the coast in your rental car every now and then and take a dip in the ocean. Rockport has been a major draw for artists since the late nineteenth century, and it’s teeming with galleries, especially around Bearskin Neck near the harbor. Five kilometers outside the village, you’ll find the jagged rocks of Halibut Point State Park, a former granite quarry whose pit quickly filled with water from underground springs. The park is popular among birdwatchers, especially in the fall and winter.

Essex

Essex is located in an area of vast salt marshes, which you can explore by canoe or kayak. Shipbuilding was once the lifeblood of the town, and that history comes to life at the Essex Historical Society & Shipbuilding Museum. It’s not just a museum, but also an active shipyard. Essex is famous for its many antique shops, often housed in beautiful 19th-century homes.

Ipswich

Near Ipswich stands Castle Hill on the Crane Estate, an impressive country house that transports you back to the “roaring twenties” of the last century. There are beautifully landscaped gardens, and on some of the estate’s green lawns, you can enjoy a picnic with a view of the Atlantic Ocean. The surrounding area features several nature trails through coastal woodland leading to the white-sand Crane Beach and the smaller Steep Hill Beach next to it. The beaches and the surrounding area serve as a breeding ground for the endangered little ringed plover, and certain sections are closed off when the birds are nesting.

Salisbury

The final stop on this scenic byway is Salisbury. Have you noticed that many places here have names you’d also find in England? That’s a legacy of the English colonists. The main attraction of this Massachusetts village is Salisbury Beach, with more than five kilometers of white sandy beach.

3. Day Trip to Plymouth

Plymouth is located more than sixty kilometers southeast of Boston and is best known as the final landing site of the Pilgrims who arrived aboard the Mayflower in November 1620. They had initially anchored near what is now Provincetown at the tip of Cape Cod, but decided not to stay there and instead sailed on to what is now Plymouth. During that first winter, nearly half of the colonists died, and if they hadn’t received help from the indigenous people (the Wampanoag), it’s likely that none of the Pilgrims would have survived.

In Plymouth, there is much to see that commemorates this historic event. First of all, a replica of the Mayflower is moored at the pier in Pilgrim Memorial State Park, and the story of the Pilgrims is told at the Pilgrim Hall Museum. Drive your rental car east from downtown along Sandwich Street, and you’ll arrive at the Plimoth Patuxet open-air museum, where both a 17th-century Pilgrim village and a Wampanoag village have been reconstructed.

4. Road Trip Through New Hampshire

Boston is close to the border with New Hampshire, so you can easily take a road trip from the city in your rental car through this neighboring state, which features waterfalls, lakes, and gorges. A wonderful tour where you can fully enjoy the beautiful natural scenery!

Portsmouth

On the first day, drive to historic Portsmouth. Along the way, you can stop in Salem, the “witch town” we described above. For a refreshing dip in the ocean, you can also drive to Hampton Beach, though it can be difficult to find parking there on hot days. Strawberry Banke is a historic neighborhood in Portsmouth, and its restored 17th- and 18th-century homes feature interiors from various eras. Downtown Portsmouth is compact, and the harbor district in particular is very lively, with many bars, restaurants, and outdoor seating in the summer. At Albacore Park, you can tour the interior of a submarine.

Mount Washington Auto Road

It takes about an hour and a half to drive from Portsmouth to Conway. Of the sixty covered wooden bridges in New Hampshire, you can admire two here, both originally built in 1890: one over the Saco River and one over its tributary, the Swift River. Another half hour further north brings you to Green’s Grant, where a fantastic road begins leading to the summit of Mount Washington, which, at 1,917 meters, is the highest mountain in New England. Be sure to check the weather conditions thoroughly before setting out on the Mount Washington Auto Road. Also keep in mind that it can get quite cold at the summit. It’s not just at the summit that you’ll enjoy the view; along the way, there are plenty of spots to pull over in your rental car and take in the fantastic scenery.

Glen Ellis Falls

On the way back to Conway, don’t miss Glen Ellis Falls. The turnoff to the waterfall parking lot is one kilometer past the Pinkham Notch Visitor Center. Don’t drive too fast, or you’ll miss the turnoff before you know it. It’s about a five-minute walk to the waterfall, but you can also take a longer hike—for example, to Wildcat Mountain, which is a ski resort in the winter.

Kancamagus Scenic Byway

Conway is located on the eastern edge of the White Mountain National Forest. This is where the Kancamagus Scenic Byway begins, offering breathtaking views of the White Mountains, the Swift River, and Rocky Gorge. Be sure to set aside time for hikes to Sabbaday Falls, Champney Falls, and Lower Falls. Also, stop by the Albany Covered Bridge, a wooden bridge built over the Swift River in 1858. Especially in the fall, the Kanc —as the route is commonly known—is a stunning road to drive, thanks to the beautiful fall colors of the leaves on the trees. This main route can get very busy, so it’s a good idea to take a detour, for example onto Bear Notch Road (closed during the winter months). Or park your rental car and take a walk through this nature reserve. There are hikes of various lengths and difficulty levels. For example, the Forest Discovery Trail is great fun for children, as they learn a lot about the forest from the informational signs.

Incidentally, this is also a beautiful route to drive in the summer, and you’ll have a better chance of finding a parking spot at the various overlooks, such as Hancock Overlook. The end point of the scenic byway is in Lincoln or North Woodstock. If you have to choose between the two, we’d recommend the latter, which has retained a much more village-like atmosphere than Lincoln. It’s a great place to spend the night before continuing your journey the next day in your rental car. The Whale’s Tale Waterpark, just north of both towns, is a fun stop for kids.

Flume Gorge / Avalanche Falls

About a ten-minute drive north of Lincoln and North Woodstock, you’ll arrive at the huge parking lot of the Flume Gorge Visitor Center. From the visitor center, a hiking trail stretching over three kilometers winds past interesting stops and unique views. Along the way, you’ll see gigantic boulders left behind after the glaciers melted, two covered bridges, a natural pool, the deep Flume and Liberty Gorges, the Avalanche Falls, a bear cave, and a wolf den. There are several shelters with benches along the trail, perfect for taking breaks. For some people, the route can be a bit challenging, as it involves walking uphill and there are many stairs. If you walk briskly, you can cover the distance in an hour and a half, but of course, you’ll want to take your time to take in the beautiful natural scenery and take photos. In that case, the hike can easily take three hours.

Squam Lake / Lake Winnipesaukee

From North Woodstock, take Eastside Road (Route 175) south. This is more scenic than Interstate 93, and you’ll occasionally drive right alongside and across the Pemigewasset River. That name means “fast stream” in the language of the indigenous people, and you can really see why in the spring when a lot of meltwater is flowing. There are a few spots where you can swim among the rocks in the river, such as at Staple Rock Park and at Livermore Falls, just north of Plymouth.

Route 175 ends at Squam Lake, where a covered wooden bridge spans the Squam River on the west side. Built in 1990, it’s nowhere near as old as other wooden bridges. Squam Lake is a wonderfully peaceful lake, and the local authorities are keen to keep it that way. Around the lake, there are only four spots where you can launch a canoe or kayak, and motorboats are allowed only if they have a limited engine capacity.

Nearby Lake Winnipesaukee is the largest lake in New Hampshire and is much more developed for tourism, especially in Meredith and Laconia, where there is a large beach. The lake contains no fewer than 264 small islands, and it’s fun to explore them by canoe, kayak, or aboard the steamship Mount Washington. A tour in historic train cars departs from Meredith.

Merrimack Valley

On the way back to Boston, you’ll drive through the Merrimack River Valley, which is the perfect area to pull over every now and then, hop on a bike, or go for a long hike. Many trails follow the route of a former railroad line, and in winter, you can go cross-country skiing there. A popular route is the fantastic Bruce Freeman Rail Trail from Concord through Lowell to Framingham. There are several places where you can park your car and rent a bike to cover part of the route. Other beautiful routes include the Nashua River Rail Trail and the Methuen Rail Trail between Lawrence and Manchester. There are also countless mountain bike trails in the region’s various state forests.

5. Mohawk Trail and the Berkshires

Western Massachusetts is known for its gently rolling hills, which, although less dramatic than the mountain ranges of Vermont or New Hampshire, also offer sweeping views. As fall sets in, the Berkshire Mountains are the place to admire the vibrant colors of fall. Winding roads run alongside lakes and rivers and through mountains lined with trees that seem to be ablaze, particularly maples, birches, and beeches. Keep in mind, however, that the trees in Massachusetts change color a few weeks later than in the states further north.

Drive your rental car west from Boston on Route 2 (or 2A). From Greenfield, this becomes the Mohawk Trail, a road that follows the path Native Americans once used to travel between the Connecticut and Hudson River valleys. The road is considered one of the most scenic routes in the U.S., with many points of interest. Just past Charlemont, right beside the road, stands the “Hail to the Sunrise” statue—a bronze sculpture of a Mohawk Native American stretching his arms toward the east. From the highest point, Whitcomb Summit (665 m), you can see far into southern Vermont and New Hampshire. Dense forests and state parks alternate with countless charming towns and villages, and the entire region boasts a vibrant arts and culture scene. For example, North Adams is home to the renowned Museum of Contemporary Art, usually abbreviated as MoCA.

North Adams / Mount Greylock

North Adams is the perfect starting point for a road trip through the Berkshires in your rental car. On the east side of town lies Natural Bridge State Park, a natural white marble bridge formed by the waters of Hudson Brook. Other marble formations include Noisy Cave and Peter Pan’s Peephole. West of downtown, Notch Road leads to the Mount Greylock State Reservation. The mountain after which this nature reserve is named stands 1,063 meters tall, and during the summer months, you can enjoy a lovely picnic at the summit with a fantastic view. Want to be a little more active? There are over 100 kilometers of marked hiking trails.

Outdoor activities for all ages

You can leave the park via Rockwell Road and then take Route 7 south. Just before you reach Pittsfield, you’ll see a turnoff for Jiminy Peak. The adventure park of the same name features zip lines and lifts to higher elevations, where you can zoom down on very long slides. There are also mountain bike trails, which turn into ski trails in the winter. The nearby Ramblewide Aerial Park is even more challenging, but it’s only open from April through October.

Lenox

In and around Lenox, wealthy industrialists built their summer homes during the 19th-century “Gilded Age,” a period of economic prosperity following the American Civil War. Thanks to the influx of money, Lenox flourished culturally and also became a popular tourist destination. In the small and charming town center, you’ll find many art galleries, chic clothing boutiques, cafés, and restaurants. Just south of town stands the imposing mansion known as The Mount, where the writer Edith Wharton lived. There, you’ll get a good sense of just how luxuriously she lived.

Stockbridge

Almost every town in the Berkshires hosts a farmers’ market during the summer months, and Stockbridge is no exception. Here, the market is held on Thursdays; in Lenox, on Fridays; and in Pittsfield, on Saturdays. Stockbridge has a really nice museum dedicated to illustrator Norman Rockwell, who drew the covers of the *Saturday Evening Post* for many years. Even if that doesn’t ring a bell, the museum is worth a visit, as Rockwell depicted everyday scenes with a healthy dose of humor.

Monument Mountain

As you drive along Route 7 toward Great Barrington, you’ll pass the parking lots where trails to the summit of Monument Mountain begin. This quartzite mountain not only offers beautiful hikes and spectacular views from the top but also carries a wealth of history. It was a sacred mountain to the Mohicans, where they left stone offerings, creating a monument. That monument was destroyed by settlers but was later rebuilt near the Mohican Monument Trail. A side trail leads to the summit at an elevation of 1,642 feet (500 meters).

Jacob’s Ladder

For the return trip to Boston, you can once again drive along a scenic byway between the picturesque towns of Lee and Russell: the sixty-kilometer-long Jacob’s Ladder. You’ll pass through several historic towns, such as Becket, Huntington, and Chester, and in between, you’ll drive on a road that was built in 1910 specifically for those new horseless vehicles. The hilly landscape is beautiful. Just past Russell, you can go canoeing, kayaking, and tubing on the Westfield River.

Why Rent a Car in Massachusetts

We hope that the five road trips listed above have inspired you to rent a car in Boston or elsewhere in Massachusetts to explore this stunningly beautiful American state. Of course, you don’t have to stick strictly to the routes. Massachusetts is at its best when you veer off the main roads and wander down small back roads. Take your time driving along back roads and country lanes, and enjoy the ever-changing views. Stop regularly to enjoy the abundance of fresh produce: delicious fruits and vegetables straight from the farm, and seafood along the coast. And what do you need to enjoy Massachusetts this way? Exactly—a rental car!