Best Time of the Year to Visit Boston

Throughout the year, Boston offers a wealth of fascinating and memorable experiences for newcomers and visitors. Whether you’re looking to explore its vibrant local culture, experience the excitement of professional sport first-hand, or get up close and personal with history, Boston has something for everyone. The only question is, when should you go?

The truth is, there’s no right answer: at any time of the year, the City on a Hill has more to do, see, taste and discover than there is time to explore it all. That doesn’t make it any easier to choose, though, which is why AAA has rounded up some essential advice and tips on what’s available in every season. Below, find out more about what to look forward to in Boston throughout the year.

Springtime in Bloom (March-May)

Springtime in Boston often starts uncertainly, with high chances of rain, snow and cold weather left over from the winter. But once it’s past that point, the season becomes one of the area’s loveliest, as the city’s numerous parks, gardens, arboretums and natural scenery turn to vibrant green. Temperatures hover between 30 and 60 °F, balmy enough to get outside and explore, but cool enough that you may need to pack a jacket to stay comfortable. It’s also a good idea to dress in layers and bring a raincoat — Spring sees some of the city’s heaviest rainfall.

Spring is also when Bostonians kick off the year with a variety of activities found nowhere else. Sports and athletics fans, for instance, can join in the opening of the MLB season on Opening Day at Fenway Park in late March or early April, or participate in the Boston Marathon. March is also when the city’s famous St. Patrick’s Day parade takes place, celebrating the city’s extensive Irish heritage.

And for those interested in culture, Spring is when a slew of must-see events take place, including the Boston International Film Festival, Art in Bloom at the Museum of Fine Arts (both in April) and the Boston Calling music festival in May.

Summer: Fun Under the Sun (June - August)

Beginning in June, Boston starts to come into its own as temperatures rise, rainfall drops off and the city’s tens of thousands of college students take a break, leaving plenty of space for visitors. Summertime high temperatures rarely exceed 80 °F, warm enough to bask in the sun, but not so hot as to force you to seek shelter in the shade.

Life in this port city has always revolved around the harbor and summer is no exception. When the weather warms up, you can take a guided walking tour around the waterfront, take a cruise or join a whale-watching excursion or simply relax with a cool drink at one of the many harborside bars and restaurants.

Step back from the water’s edge; there’s even more to do in town. While spring has St. Patrick’s Day, summer has the North End Feasts, a series of celebrations, featuring delicious food and live entertainment, held to honor a variety of Catholic saints by Boston’s Italian-American community. It’s also a great time to catch a few concerts, with paid and free live music found at locations like the waterfront, the Public Library and venues across the city.

For history lovers, summer is also peak season, as many sites and attractions open up around this time of year. For example, June to October is widely considered to be the best time to walk the Freedom Trail, a free walking tour taking in such significant sites as the USS Constitution, Faneuil Hall and the Bunker Hill Monument. Anticipating an influx of curious visitors, many of Boston’s most renowned historical sites put on new exhibits and offer a wider range of tours and activities to transport you back in time to when the city was at the heart of the country’s founding.

Avoiding crowds while visiting is largely a matter of planning: whenever possible, book ahead for events you want to enjoy and try to leave your hotel either early in the morning or after the morning rush hour. You can also find a variety of hidden gems like local cafes and shops by checking with the city’s Visitors Bureau. It’s important to note that Boston is infamous for its unpredictable summer weather due to rapidly-shifting winds off the ocean, so pack a few spare warm garments and a raincoat and plan some indoor activities for your stay.

Fall Foliage: A Kaleidoscope of Colors (September - November)

If you’re eager to discover why Boston is considered one of the most walkable cities in the country, fall is the ideal time to visit. Massachusetts autumn days are crisp, warm and dry, making the season perfect for taking in the brightly-colored foliage at Franklin Park, the Public Garden, or Arnold Arboretum in nearby Cambridge. And if you want to experience New England's legendary fall foliage, this is a great time to take a road trip to the charming colonial towns ringing the city.

Fall is also when Boston’s traditional favorite foods shine. The cool, clear weather is the perfect setting for enjoying a meal of old-fashioned Boston baked beans, clam chowder, or roast beef sandwiches. And when you’re in the mood for something sweet, look for pumpkin bread, fresh apple cider, or maple doughnuts from one of the city’s many beloved bakeries.

Many of Boston’s best summertime activities are still an option well into the fall, but there’s plenty more to experience when the air turns cooler. Boston’s Black Heritage Trail, the Salem Witch Museum and the Blue Hills are all fall favorites for Bostonians, plus it’s an excellent time of year to catch a Red Sox game at Fenway Park. And if you’re looking for somewhere warm and dry to spend a wet autumn day, you can’t go wrong with visiting the original Cheers bar, directly across Beacon Street from Boston Common.

Winter Wonderland: (December - February)

Winters in Boston can be a shock for the uninitiated, with freezing temperatures and heavy snowfall throughout the season. But those same qualities make it a great destination for holiday fun, with snowy cobblestone streets, delicious wintertime foods and a surprising array of choices when it comes to fun activities.

Temperatures around this time of year are often between 20 and 30 °F, so you might want to wait to take walking tours in town. It’s also a good idea to pack extra sweaters, a heavy winter coat and warm boots to stay comfortable. However, the city has an excellent transportation system giving visitors access to all the museums, theaters and indoor shopping venues you could hope for, as well as the surrounding towns and cities.

Top wintertime attractions in Boston include Hanukkah and Christmas celebrations at Copley Square and Boston Common, as well as cold-weather festivities like the Boston Winter Holiday Market at City Plaza Government Center or SoWa Winter Festival at SoWa Open Market. Plus, for music lovers, there’s the Boston Holiday Pops in December.

Boston's Year-Round Gems

A lot of the activities and attractions mentioned here can be enjoyed all year long. Simply put, Boston has too much to offer to fit it all into one or two neat seasons. The city is home to cultural destinations like the Museum of Fine Arts, the Institute of Contemporary Art and the world-famous Isabella Stewart Gardner Museum. Also, open for business throughout the seasons are countless restaurants, cafes, bakeries and bars offering everything from Boston baked beans to fish and chips, cannolis and classic Boston cream pie.

Sports are also a great year-round option. From spring to fall, the Red Sox play dozens of home games at Fenway Park; from October to April, hockey fans can catch a Boston Bruins game, while basketball lovers can watch the Celtics show off their skills. Visiting soccer aficionados can also check out the Boston Bolts, while sports fans of all kinds can’t afford to miss any of the top-ranked college teams representing Harvard, Northeastern and Boston Universities.

Ultimately, the best time to visit Boston is up to individual taste, with plenty on offer year-round to satisfy everyone and a distinctly different character in every season. Whenever you choose to visit, you can count on AAA to provide all the expert advice you need and to help you find the best deals on lodging, activities, meals and more.

Join the over a million people who are AAA members and start planning your trip to Boston today. Dream up the perfect trip with our Trip Canvas research tool and use your membership to get the best discounts on hotels, rental cars and entertainment tickets.