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12 “Wicked Good” Places to Visit in Boston

Boston, once visited, is a city that isn’t easily forgotten. Filled with rich, early-American history, Beantown is fun for all ages. So, as the Bostonians would say, “Grab a coffee from Dunks” and check out these “wicked good” places to visit.


Winni Wanderer | Spotlight Boston

Castle Island


Castle Island is a true hidden gem in Boston and definitely a MUST see if you’re visiting Boston in the spring, summer, or fall. Castle Island is located at the northern tip of South Boston and anchors Pleasure Bay, which offers 22 acres of beautiful beach and city views. This destination does not disappoint. Not only does it offer free parking for all visitors, it is a great spot for family activities like walking, swimming, bike riding, fishing, kayaking, looking for shells and crabs, and playing on the playground. Pack a lunch or grab some ice cream and/or seafood from the iconic ‘Southie’ landmark, Sullivan’s, located right on the island! Picnic tables are available to sit and eat, or to enjoy watching airplanes from Logan airport take off and land. Historical Fort Independence is also located at the top of the island, open to explore in the summer, and it offers gorgeous views while overlooking the Boston Harbor.

 

Boston Common & Public Garden


Winni Wanderer | Spotlight Boston

The Boston Common (America’s oldest park) and Public Garden (America’s first public botanical garden) are definite go-tos when visiting Boston. The Boston Common is a great place to visit at all times of the year. The Frog Pond is located in the center of Boston Common; it is a great way to cool off in the summer and fun for ice skating in the winter. The Public Garden is stunning during the summer months; it is filled with unique botanicals that you typically wouldn’t see on a daily basis. The swan boats are also located in the Public Garden and offer a fun, leisurely ride that brings you under the beautiful walking bridge and willow trees. Pack a lunch or enjoy the best fried dough, Grillo’s pickles, ice cream, lemonade, or sausage from many concession stands to choose from!

 

Faneuil Hall Marketplace


Faneuil Hall is one of Boston’s most well-known historic sites. When you visit Faneuil Hall, you are actually visiting four amazing places at once: Faneuil Hall, North Market, South Market, and Quincy Market! The variety of entertainment, dining, and shopping is endless. In fact, there are 36 food vendors and 14 restaurants to choose from, making this the largest food hall in New England. If you love to shop, you’ll love that Faneuil Hall Marketplace has over 100 shops and pushcarts. Outside, you’ll find live music and some street magic shows, comedy, and even dancing. Bring your sneakers because this destination is a cobblestone promenade that you’ll want to visit. Great for family days, date nights, or even just exploring a little piece of Boston.

 

Freedom Trail

Winni Wanderer | Spotlight Boston

The Freedom Trail, where every step tells a story, is the most popular tour in Boston. It highlights the American Revolution and its history along its 2.5-mile red line trail. The tours are available year round and are led by 18th- century costumed guides which make it a fun family friendly event. However, you can also experience the Freedom Trail through a self-guided tour by using a map, or audio guide. Along the way, you’ll visit 16 nationally significant historic sites and be able to explore museums, burying grounds, meetinghouses, churches, and even be able to go inside the Paul Revere House. Grab your sneakers, follow the footsteps of America’s founding fathers and experience over 250 years of history—you won’t regret it!

 

Prudential Center


Enjoy the day in Back Bay Boston! Experience a full day of all you can eat, drink, and shop at this indoor shopping mall, with over 75 boutiques, restaurants, high end stores, and entertainment for all ages. Eataly is located right in the Prudential Center and is an incredible Italian marketplace with a variety of bistros, bars, imported specialty pasta, and you can even take it to go. It’s a great place to experience and enjoy delicious Italian treats. The Skywalk bridge connected to the Prudential Center takes you across the street to Copley Place which is a short walk to the famous Newbury Street, where you will find high-end boutiques and shops that sell luxury goods.. The Prudential Center also has exciting plans to open up “The View” in 2023, which will offer a breathtaking 360-degree view of Boston from the very top of the Prudential, as well as an incredible dining experience! This makes for a great day trip into Boston, or even a weekend away that you’ll never forget.

 

Charles River Esplanade

Winni Wanderer | Spotlight Boston

The Charles River Esplanade, or as Bostonians would say, the Esplanade, is a beautiful 17 mile stretch of paths along the banks of the Charles River. This is a great place for walking, biking, jogging, rollerblading, canoeing, kayaking, and other activities. The possibilities there are endless. There is a community boat launch, sitting areas, a playground, cafe, walking bridges, and the famous Hatch Shell, where movies, performances, concerts, and the Annual Fourth of July Fireworks Extravaganza take place! Not only can you enjoy the summer there, but you can also ice skate, and enjoy a winter stroll as well. Come soak up the sun along the Charles, or enjoy a concert at the Hatch Shell, you’ll enjoy the views and community there.

 

North End The North End, also known as Boston’s Little Italy, is home to a variety of historical sites and many of the most popular Italian restaurants in town. You’ll want to visit one or more of the famous eateries in this neighborhood for some homemade pasta, freshly baked bread, and amazing coffee. This is a great spot to visit in the summer months when the cobblestone streets are filled with live music, parades, Italian filled pushcarts, and even street performers. Although the North End is known for its delicious and authentic Italian food, there are shops on Hanover Street in the North End where you can find some boutiques, floral shops, and ice cream. Bring your appetite when visiting the North End in Boston, and don’t forget to admire all of the diamond panes on the old buildings!

 

Fenway Park

Winni Wanderer | Spotlight Boston

Fenway Park is home to the Boston Red Sox and is the oldest active ballpark in Major League Baseball. Fenway is one of the best-known sports venues in the world. Experience Fenway Park by attending a baseball game, a concert, or a guided tour. The guided tour will teach you about many legendary moments and player history, and it will give you a spectacular view atop the 37-foot high, Green Monster. Fenway Part is conveniently located along Landsdowne Street, home to sports bars, the House of Blues, pubs, and Boston’s ONLY country venue, Lorettas Last Call, offering authentic southern food, country music, and line dancing! This street is nothing but a good time.

 

Samuel Adams Brewery & Taproom

Samuel Adams Boston Brewery is the original home of Samuel Adams and located in the heart of Jamaica Plain. Today, it is a fun place to grab a beer, and explore the innovation, research, and development of the brewery through a variety of guided tours. The Samuel Adams Taproom is a huge new addition to downtown Boston, and it is only a few feet away from the iconic Samuel Adams statue. It offers 3 floors of dining and seating, including the popular outdoor rooftop deck, allowing for 15,000 square feet of beer gatherings.

 

Lawn on D

The Lawn on D is an unforgettable venue that is always full of life and entertainment. This is Boston’s most dynamic and innovative event space, great for all ages. The Lawn on D is only open in the summer, so enjoy the public events and book your private events while it’s open. You will not regret it. It is such a unique space filled with large circular light up swings big enough for adults and kids. There is also corn hole, a variety of large yard games, a food and drink concession stand, bar, stage for local bands and live entertainment, and scheduled public events. Enjoy the community and fun at the Lawn on D!

 

Rose Kennedy Greenway

Winni Wanderer | Spotlight Boston

This is a smaller, yet amazing spot in Boston that you can’t miss. The Rose Kennedy Greenway is a one-mile strip of greenery, gardens, promenades, and the most loved cool off and splash area, the Rings Fountain. It is a great linear path to walk through in the spring, summer, and fall months. You’ll find food trucks, concession stands, and the new Trillium Beer Garden on the Greenway. It is Boston’s first open-air beer garden! There is also plenty of free entertainment along the Greenway including live concerts. It is a great spot to just relax for the day or bring the family for a stroll through the city.


 

Museums & Tours

There are so many museums and fun tours you can do in Boston as well, here are a few of the most popular ones: Boston Children’s Museum, Museum of Science, Museum of Fine Arts, Boston Public Library, New England Aquarium, Duck Boat Tours, Isabella Stewart Gardner Museum, New England Holocaust Memorial, USS Constitution Museum, Boston Tea Party Museum, and many more! Tickets are needed for all these locations so be sure to check out information online in advance.

 

We hope these must-see places have inspired you to plan a visit to Boston. Did we miss any of your favorite places in Beantown? Drop us a note at WinniWanderer@winni.com and tell us, because hearing from you will make our day!

 

By Staff Contributor

 

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