The Best Landmarks in Eastern Massachusetts: Things to Do in Boston in the Winter

The Best Landmarks in Eastern Massachusetts: Things to Do in Boston in the Winter

Freedom Trail

Boston is a top city to visit in the United States in terms of the country’s history and notable landmarks. The Freedom Trail stretches about 2.5 miles in parts of Downtown Boston to the Northern side of the city which includes historical landmarks that originated as far back as the 16-1700s and were crucial to shaping us into the nation that we are today. The trail includes landmarks like the Granary & Copp’s Hill Burying Ground, the Boston Massacre Site, and the Bunker Hill Monument. The Boston Common, which is the nation's oldest public park, is also located along the trail.

The iconic trail is home to a total of 16 nationally significant historic sites. The Freedom Trail shop on the trail has many different souvenir and clothing options for you to remember your visit and the experiences you had. My favorite landmark on the trail is the Boston Massacre Site where you can stand and see the exact pinpoints where Bostonians and Redcoats clashed in the streets. Had this not taken place, who knows, we may have still been a part of Great Britain today!

USS Constitution | USS Constitution Museum

The USS Constitution is the world's oldest commissioned battleship that is still afloat. It is still docked at the Charlestown Navy Yard and it was constructed in the 1790s but played a crucial part in the War of 1812. It was involved in several other major events including the First Barbary War, The Africa Squadron, The Quasi-War, and more. The engaging exhibits, interactive displays, and tons of interesting artifacts make up most of what the museum offers, including information about the sailors who served on it. Museum and ship admission are cheap at only $10-$15 for adults and $5-$10 for children. Though the history of it goes way back, the actual museum started in 1972 and the museum also includes a gift shop, mini golf course, and a food/drink spot!

Harvard & Massachusetts Institute of Technology (MIT) Campuses

Harvard and MIT are two of the most famous colleges that are recognized globally. The Northeast region of the United States is home to some of the smartest and most prestigious universities on the planet. Both of these colleges have tours and visits that you can access through their websites to see specifically what they have to offer. Both located in the suburb of Cambridge, Harvard’s campus is further West down the Charles River and features more of an older look that is supposed to represent Boston's history and significance. MIT’s campus is further East down the Charles River right across from downtown Boston and has more of a modern and urban feel with some taller buildings that make up the college. If you are in or are planning to be in a field surrounded by computer science, engineering, healthcare, or economics, visiting these two colleges could definitely be something that can provide value to your career or general understanding of those topics!

Boston Tea Party Ships & Museum

Located right off of the Boston Main Channel near the harbor in downtown Boston lies where the Boston Tea Party took place. Now they have an official museum with the tea ships docked right next to it. The museum is small but hosts 8 different sections that each focus on a specific part of the event. The official tour of the museum typically takes about an hour in total to complete and there is also a gift shop at the end. The Boston Tea Party is one of the most important events in the history of our country and many parts of this great museum have interactive exhibits that provide visitors with content that very well displays the importance of it all. Another optional activity that tourists can participate in is historical reenactments where visitors get the opportunity to toss tea into the harbor just like the colonists did in 1773.

Ascend Cannabis Dispensary | Downtown Boston

Ascend is a very large and luxurious cannabis dispensary in the heart of Boston. The wide range of cannabis products and local sourcing, manufacturing, and testing are a core reason why the brand is so popular in Massachusetts. The three main cannabis brands that the store thrives on selling are Ozone, Royale, and Simply Herb. The store features a fairly modern look with greenery and other cool decorations on the inside. The inside also has many different sections of the store that have different checkout stations and knowledgeable workers that can help you get what you are looking for. Many locals describe the establishment as one that offers “excellent value for the cost” and has frequent promotions or sales with others expressing their enjoyment of the loyalty program.

Celtics Game | TD Garden

Depending on the specific time of the winter season, you could be able to catch a Patriots game in Foxborough as well if they are in town! Sports fans know the city of Boston and its people have one of the most passionate fan bases in the nation. The Celtics, Patriots, and Red Sox are all historically top franchises in their respective leagues, especially the Celtics. Thriving off of their recent NBA finals victory in 2024, the Celtics are still a top 3 team in basketball through the halfway point of the 2024-25 season with tons of great and young talent along with crazy fans that help sell-out the arena and remain as one of the top teams in the NBA in attendance. A recently published article by ESPN titled “2024-25 NBA Arena Rank” has TD Garden in 4th place, with many other online blogs ranking them in the top 3 based on atmosphere and amenities.

Salem Witch Trials Memorial

An interesting museum that features one of the oldest events recognized by the area (1692), the Salem Witch Trials memorial/museum located in Salem, Massachusetts, about an hour North of Boston has many interesting things to see. The design of the memorial is truly special which features granite benches that have the names of each accused individual carved into them. The trial records from the event were also recorded and have quotes from the accused individuals written down in different areas of the memorial. The area is also surrounded by black locust trees since those types of trees were believed to be the same trees that judges, town officials, and law enforcement used to hang the victims who had been accused of practicing witchcraft. The memorial is home to the old burying point cemetery, one of the oldest cemeteries in the state, where many of the victims were buried.

North End | Boston’s Little Italy

North End is an Italian-themed neighborhood in Boston right on the harbor near downtown. The old brick architecture, narrow streets, Italian immigrants, and Italian restaurants will make you feel like you are in Italy (minus the weather). The North End is also known for its incredible nightlife with no shortage of bars, pubs, and other entertainment venues. The Italian dining options in the neighborhood have quality dishes with price ranges that are fit for those on a budget or those looking to spend some extra cash. Some of the most popular restaurants in the area are Carmelina’s, Trattoria II Panino, and Giacomo’s Ristorante. Cantina Italiana is another iconic restaurant with entrees ranging from around $12-$25. The North End also features lots of special events and celebrations. Unfortunately, most of those take place in the Summer when the weather is nicer.

Ice Skating at Frog Pond

Ice Skating at Frog Pond in Boston Common is a must-do in the winter. Boston Common is a large park located in the Western part of downtown with many fun or relaxing activities in the warmer part of the year, but the pond in the middle area of the park gets turned into a skating pond during the winter season. They stay open as late as 10:00 pm on weekends and open at 10:00 am every day. The feeling of learning how to skate and getting better with time will be worth it once you get to experience what it is like to fly around the pond while you enjoy the view of downtown as well as the rest of the beautiful park!

Conclusion: Best Things to Do in Boston in the Winter

Thank you for reading “Best Things to Do in Boston in the Winter." Boston, one of the Northeastern region's top cities, is very used to cold weather. Similar to New York, the city is very suitable to visit in the freezing cold months like December or January (unlike many other areas of the country), making it stand out. The rich history of the city, diverse culture, large sports scene, and prestigious universities truly shape Boston into the city that it has become. The architecture of the older but renovated areas of the city using brick and cobblestone on the buildings and streets gives the city a unique look and helps it stand out.

By: Drew S.