From the Red Sox to the Patriots, Massachusetts is famous for its sports teams and their diehard fans. Experience the action on an adventure-filled road trip through Boston and beyond.
Massachusetts is the thriving cultural capital of New England. The leafy, historic state is home to the charming islands of Martha’s Vineyard and Nantucket, colonial architecture, winding cobblestone streets and residents proud to have survived a couple of hard winters in their day — but even prouder of their home teams.
Sports are a way of life — a religion even — in Massachusetts. The Red Sox went 86 years without winning a World Series baseball championship, but devoted fans never lost hope, or passion. From the team's home at Fenway Park to the Head of the Charles Regatta and the Patriots Hall of Fame, here’s how to spend five days experiencing the best of the state’s sporting heritage.
Begin in Boston, starting at Fenway Park. Opened in 1912, it's the oldest active ballpark in Major League Baseball and one of the oldest stadiums in the world. You can watch a game without a ticket at Bleacher Bar, which provides an unobstructed view of centerfield from beneath the bleachers, in a space once used as the batting cage for visiting teams. For an immersive experience, stay at Hotel Commonwealth, the official hotel of the Red Sox, where rooms are decorated in tribute to past players and triumphs.
Next, take the green line on the Massachusetts Bay Transportation Authority (MBTA) to TD Garden, an arena home to the Boston Bruins ice hockey and Boston Celtics basketball franchises. Take a photo beside the statue of hockey legend Bobby Orr and check out the half-mile of exhibits at the venue's Sports Museum. Enjoy dinner at the nearby Banners Kitchen & Tap, which features a near-40ft LED screen, plus 52 television sets showing different matches.
Head to Copley Square, on Boylston Street, to see the finish line of the prestigious Boston Marathon — the world’s oldest annual marathon, first run in 1897. Then walk north to the Charles River basin, at whose west end is the Boston University Bridge. This is the start point for the Head of the Charles Regatta, a three-day rowing competition that's drawn world-class talent since 1965. Less than an hour's walk from the bridge, the nautically inclined can rent a kayak or a sailboat from Community Boating, one of the United States' oldest public sailing organisations (established in 1946).
A 75-minute drive southeast takes you to Cape Cod. In the summer, check out the Cape Cod Baseball League, the premier American amateur baseball league, which has been a springboard for many all-stars in the sport. The area is also home to the Falmouth Ice Arena, one of Massachusetts’ many skating venues.
For a scenic stay, book a night at the Inn on the Sound, a charming oceanfront B&B with sweeping views of Vineyard Sound, the ocean stretch that separates Cape Cod from Martha's Vineyard.
After a morning swim at the Inn on the Sound, drive northwest for an hour to Foxborough. The town is home to Gillette Stadium, home of the New England Patriots, whose 11 Super Bowl appearances and six wins are a source of local pride. Be sure to visit the Patriots Hall of Fame, where stars such as Tom Brady are celebrated.
An hour west is Worcester, Massachusetts’ largest city after Boston. Enjoy lunch in a vintage wooden booth at George’s Coney Island, a local institution that has served its signature hot dogs for more than 100 years in a retro setting, winning many accolades along the way.
Head to Polar Park to cheer the Worcester Red Sox, known as the WooSox and a minor league affiliate of the Boston Red Sox. The stadium’s laid-back intimacy — its capacity a quarter of Fenway Park's — makes for a relaxed evening of baseball and beer. At the end of the evening, turn in at the luxurious Beechwood Hotel in the heart of Worcester.
Come the morning, drive an hour west to Springfield. The city is the birthplace of basketball, created by a YMCA athletics instructor and first played in 1892. At the three-storey, 48,000sq ft Naismith Memorial Basketball Hall of Fame, you can shoot hoops in historic baskets. Dine on burgers and steak at the nearby Max Tavern, then drive 15 minutes north to Holyoke — the birthplace of volleyball — to check out the International Volleyball Hall of Fame.
Alternatively, drive an hour northwest to Jiminy Peak, the largest ski area in the state. Purchase a four-hour lift pass and enjoy sweeping views of the Berkshire Mountains. Afterwards, relax with some upscale pub dining at the rustic and atmospheric John Harvard's Restaurant and Brewery.
Head east to the idyllic North Shore. The drive from Jiminy Peak to Newbury is more than three hours but it is worth it to watch the Essex Baseball Club play with 1864 uniforms and baseball's original rules (no gloves required). Dine in nearby Salisbury at The Winner’s Circle, a 1950s-themed sports bar with billiards, an arcade and more than 70 televisions.
Those raring to get outside after a few days of driving can explore the 2,000-plus-acre marsh of the North Shore's Crane Estate on a guided hiking or kayaking tour with CraneOutdoors. Rest your weary limbs in charming downtown Newburyport at the Garrison Inn, a small hotel that dates to 1809. The next day, drive less than an hour back to Boston or add half an hour or so to head south past the city to the Massachusetts Golf Hall of Fame & Museum in Norton.
