A Self-Guided Motorcycle Riding Tour of Boston

Feb 16, 2022


Boston, Massachusetts.

Perhaps more than any other East Coast city, the story of Boston makes for a long and interesting tale. Known as the “Cradle of Liberty” for being the birthplace of the American Revolution, you can feel the historical significance at every cobblestone corner. History isn’t just there to be read in books—it’s there to be felt, seen, touched, and heard. For natives and visitors alike, Boston affords this kind of close connection with the past. 

Motorcycle enthusiasts in particular are in for an unforgettable adventure. Exceptional food, world-class museums, outstanding parks, historic landmarks, and musical venues await the rider willing to put adventures in Massachusetts country on hold for a fun-filled ride through Boston’s hallowed streets. Need more tips? Read the History-Filled Motorcycle Routes Near Boston article.

If you’re searching for a safe, quick, and convenient motorcycle rental service you won’t have to look far. Check out Riders Share, grab a motorcycle rental in Boston, and have the time of your life on one of these mesmerizing self-guided tours.

1. Boston—North End

The North End is surrounded by a lot of historic sites, which makes it a great introduction to Boston’s past. The North End, Boston’s own Little Italy, is a maze of narrow streets with some of the city’s oldest buildings. Located off of I-93 N, ride the highway and continue on North St. Drive. You'll spend most of your time on Hanover street: many cafes, restaurants, and historical sites are situated in or located near this road. On the self-guided Freedom Trail, tourists pass points-of-interest like the Old North Church and the Paul Revere House, which played a key role at the beginning of the Revolutionary War. For a taste of the North End’s memorable cuisine, we recommend the stylish Sicilian-inspired restaurant Carmelina's near Paul Revere's home: they serve classic Italian dishes that come with a modern flair. 

To ensure maximum ride enjoyment on every road, and in every situation, select a BMW motorcycle in Boston. The BMW S 1000 R—it's more than just an agile and fast-accelerating superbike. This model features cutting-edge and dynamically-styled racing looks. Wherever your journey takes you, the S 1000 R gets you there fast. With its superior handling and excellently-tuned suspension, the S 1000 R feels at home on the North End’s maze-like web of roads.

2. Boston—Theater District

Boston boasts one of the finest theater districts in the country. Located in the heart of the city, this district is also home to numerous performance venues and restaurants. Whether you’re looking to enjoy a Broadway musical or an avant-garde experimental play, this district has something for every type of theatergoer. Choose performances ranging from popular Broadway shows to opera, dance, comedy performances, and everything in between. Many of its theaters are located on Washington Street, Tremont Street, Boylston Street, and Huntington Avenue, all within an area that’s little more than half a square mile in size. Check out the Emerson Colonial Theater, one of the oldest continually-operating theaters in America. Riding through the heart of Boston's theater district, many nearby restaurants also offer pre- and post-theater menus to satisfy your hunger before the performance begins and allow you to continue the fun after the curtain falls. 

If you’re looking for style and power, rent a Harley-Davidson cruiser. Harley-Davidson’s FXFB Fat Bob gives decent comfort so you can focus on riding through the city. The Harley-Davidson Road King is another comfort-minded option that’s the perfect blend of design and performance. 

3. Boston—South Boston

There's a lot to see and do in this eclectic, old-school, new-chic neighborhood. Walk along the same cobblestone streets on which General George Washington himself once set foot. The beauty and history of the area will leave you with a lasting memory.  To get to South Boston or “Southie”, take I-93. Most sites are accessible off of Dorchester street. You'll find hidden gems when wandering the streets of this noteworthy neighborhood. Old-school diners and taverns mingle with pizzerias and gastropubs. Taverns like Lincoln's Tavern and Restaurant have become one of South Boston’s most popular neighborhood bars. Lincoln’s is reminiscent of old dining halls and clubs and invokes that powerful nostalgia, while also offering a hip atmosphere and a modernized menu. Just down the street and around the corner is the location of a Revolutionary War site, the Dorchester Heights monument. South Boston even offers sweeping Boston Harbor and downtown skyline views. 

If you're planning on riding a Ducati in Boston, we recommend a Monster 797. This bike was designed with the urban rider in mind, making it a well-suited choice for Boston. It’s minimalist and sculpted design makes it the perfect city bike, while its high-performance engine offers superb handling. 

4. Boston—Fenway/Kenmore

The Fenway/Kenmore neighborhood is located between The Kenmore neighborhood and north and west of Fenway, roughly separated by the Massachusetts Turnpike. This neighborhood, better known for being the home of the Red Sox, is also one of Boston's academic and cultural hubs. You can also catch a game at Fenway Park, one of the nation's oldest professional ballparks. Not far from Kenmore Square, you'll also find the Isabella Stewart Gardner Museum and  Museum of Fine Arts. The Isabella Stewart Gardner Museum is evocative of a 15th-century Venetian palace and houses a diverse collection of world-class art! Visitors can walk or relax in a beautiful skylit courtyard full of plants and flowers. Just next door is the Museum of Fine Arts, which is the 17th-largest museum in the world. It houses works of art which include masterpieces by Michelangelo, Monet, and Van Gogh.

Pick up a Ducati 1098 S sportbike in Boston for a ride that will make navigating through city traffic a breeze. With it’s incredibly light and responsive suspension, powerful engine, and strong brakes, this motorcycle offers a top-tier combination of speed and agility. The 1098 S is an incredible superbike that's crafted to deliver an exhilarating ride every single time you hop on it. 

5. Boston—Scenic Drive to Gloucester

Take a scenic drive through historic seaside Gloucester, a 400-year-old seaport known as “America's First Port.” This historic fishing port was made famous by the book "The Perfect Storm," which was later adapted into a movie of the same name. Located northeast of Boston, Gloucester is made up of scenic beaches with beautiful views. Getting to Gloucester is easy. Just take I-93 North, then take exit 28 towards RT-99. Next up, take the exit to US-1 North and merge to RT 128 North. Finally, take exit 54 to merge to Yankee division, then take the exit onto Washington Street for a 45-minute-long scenic route. Head over to a whale-watching cruise for an opportunity to see whales breaching off the coast of Gloucester (which happens to be one of the top whale-watching destinations in the world). When hopping on the boat make sure to head to the Eastern Point lighthouse. When visiting the Eastern Point Light, you’ll want to walk the half-mile jetty so you can catch some unique views of the lighthouse and enjoy a stunning panorama of the Atlantic.

Experience the exhilarating freedom of riding a Harley-Davidson motorcycle in Massachusetts. More specifically, the Harley-Davidson FLHRI Road King should be your motorcycle of choice. This motorcycle comes with a large windscreen to shield you from the elements and hard saddlebags for storing your belongings. There’s also an optional lockable rear trunk and a lightning cable so you can charge your phone. 

We hope you've enjoyed this guide and recommendations for motorcycle rentals in Massachusetts. The Boston area offers plenty of options for motorcyclists to explore one of the most historic cities in the United States. If you want to tackle additional motorcycle rides in Massachusetts, we’ve got you covered. Check out these five routes designed to take you on an adventure through all of the highlights and points of interest around Boston.