91. Shop, Dine & People Watch on Commercial Street

Commercial Street in Provincetown, Massachusetts

The main street in historic Provincetown is known as Commercial Street. Cape Cod’s vibrant street is home to numerous restaurants, bars, galleries, and shops. This is the place to stop in Provincetown for any type of food or entertainment. It’s also a great place to people watch and admire the great architecture. Visit during the summer months as some restaurants are only open seasonally. Furthermore, summertime is typically when most festivals and events take place.

Visit the Provincetown website for information regarding annual events.

Location: Commercial St. Provincetown, MA 02657

92. Take a riverfront stroll at Fall River Heritage State Park

Views from Fall River Heritage State Park in Massachusetts

This small park in Southeast Massachusetts sits on the banks of the Taunton River.  A ~mile long walking path offers excellent views of the river, the Charles M. Braga Bridge, and Battleship Cove. After your walk, be sure to stop by Jerry Remy’s Sports Bar for lunch and a game on the enormous 6½ by 11 foot TV screens! While living in Fall River, I jogged along the boardwalk at least a few days a week: the scenery is so gorgeous! Update: All Jerry Remy locations are now closed.

Location: 200 Davol St Fall River, MA 02720

93. Stroll along the beautiful Boston waterfront

Boston waterfront

While downtown, take the time to explore Boston’s beautiful waterfront area. If you are interested in a whale watching cruise, CityPass offers a great package which includes the cruise, as well as admission to the New England Aquarium, the Museum of Science, and Skywalk Observatory for one low price. This is a really great deal! Massachusetts consistently ranks among the top places in the world for whale watching. Harbor Walk is a great path for walking, jogging, or cycling while taking in the serene views. There are plenty of great restaurants in the area (Legal Sea Foods offers fabulous waterfront seating), as well as places to grab a coffee to accompany your walk.

Location: Boston, MA 02113

94. Shop, dine, & play at Providence Place Mall

Providence Place Mall in Rhode Island

You could spend the entire day at Rhode Island’s largest mall and never get bored. This urban mall features great views of the city from its numerous floor-to-ceiling windows. Inside you will find over 100 stores, 10+ restaurants, a Dave and Busters, a 16 screen theater, an IMAX theater.  The mall is clean and modern looking and usually not very crowded unless you visit during prime times. Conveniently, there is a Westin hotel connected via skywalk for guests visiting from out of town. I visit this mall frequently living just 20 minutes away. Really, I could spend the entire afternoon here with all the great dining & entertainment options. Update: The Westin has been replaced with an Omni (a much nicer hotel brand in my opinion).

Location: 1 Providence Pl, Providence, RI 02903

95. Grab a coffee and relax at Somethin’s Brewin’

Somethin's Brewin' in Lakeville, Massachusetts

In the small town of Lakeville, Massachusetts, located in Plymouth county, you will find a cozy little coffee shop called Something’s Brewin’. This comfortable, friendly shop brews organic, locally roasted coffee and offers comfortable couches and home-style décor, which changes depending on the season. The atmosphere is warm and inviting, and the coffee always excellent! This place also holds historic significance as the building was a library back in the day. Today, you can purchase used books.

Update: Unfortunately, this cute cafe closed down!

Location: 241 Main St, Lakeville, MA 02347

96. See where Hocus Pocus filmed

Max and Dani's house from Hocus Pocus, filmed in Salem, Massachusetts
The Dennison’s house from Hocus Pocus

One of my favorite things I’ve done thus far in Massachusetts has been touring the iconic Hocus Pocus filming sites. I am a big Halloween buff and this has been one of my favorite movies since long before it became a cult classic. It’s pretty cool than 90’s kids can relive their youth via a nostalgic self-guided tour of the film sites.

Check out my self-guided Hocus Pocus tour

97. Enjoy home made ice cream

The Ice Cream Barn in Swansea, Massachusetts

I have been to many local ice cream shops throughout the country during my years of traveling. New England is hands down home to the most delicious homemade ice cream anywhere. No matter where you are staying, you can find a great locally run creamery. The best? The Ice Cream Barn in Swansea – a small town about 20 min east of Providence. All ice cream is made fresh on-site and they offer a delicious assortment of flavors which vary seasonally. I love the rustic country setting.

98. Tour historic Benefit Street in Providence

John Brown house on Providence's historic Benefit Street

Take a mile long walk along one of the oldest streets in Providence. You will be treated to some of the best colonial architecture in the US. This cobblestone walkway is often referred to as the “Mile of History” as some of the oldest US attractions are located along this road, including the 4th oldest library (The Providence Athenaeum) and the oldest running little theater (Barker Playhouse). I loved just strolling around and taking pictures of all the historic sites.

Location: Benefit St. Providence, RI 02903

My self guided tour of Benefit St.

99. Head to Boston Common for the annual tree lighting ceremony

Boston Common Christmas Tree

The Boston tree lighting ceremony is a fun, festive event for the entire family. Each year various entertainment acts, including popular singers from shows such as American Idol, come to Boston Common for one of the country’s best tree lighting ceremonies. To add to the excitement, the Skating Club of Boston hosts a free ice skating performance prior to the lighting. Zoo Lights, a festive seasonal ice skating rink, and seasonal productions such as The Nutcracker give endless opportunities to get into the holiday spirit! Boston in the winter is truly a magical place with the snow, festive lights, and holiday happenings.

Location: 131 Tremont St, Boston, MA 02111

More Christmas fun in the Boston metro

100. Take a summer break at Horseneck Beach

Horseneck Beach in Westport, Massachusetts

This extremely popular South coast beach, located in Westport, features some of the biggest waves in the state. Swimming here is fun because of the humongous waves, however, it tends to get very crowded so plan for a weekday visit if possible.

Location: Rt 88 Westport, MA 02790