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Weekend Trip To Boston: What To Do


Modified: January 3, 2024

by Gilbertine Durbin



Welcome to Massachusetts, a state steeped in history and brimming with charm. Nestled in the heart of New England, the Bay State offers a wealth of attractions and activities for visitors to enjoy. One of its standout destinations is the vibrant city of Boston. Whether you’re a history buff, an art enthusiast, a food lover, or simply seeking a weekend getaway, Boston has something for everyone.


Steeped in American history, Boston is a city that effortlessly combines the old with the new. Its iconic landmarks, such as the Freedom Trail and Paul Revere’s House, will transport you back in time to the early days of the American Revolution. But Boston is not just a city of historical significance; it’s also a bustling metropolis with a thriving arts scene, world-class museums, beautiful parks, and a vibrant culinary landscape.


When planning your weekend trip to Boston, be sure to allocate enough time to explore the city’s historical sites, visit its renowned museums and galleries, indulge in the local cuisine, and soak up the atmosphere of its charming neighborhoods. From the cobbled streets of Beacon Hill to the energetic vibe of Fenway, Boston offers a diverse range of experiences that will leave you captivated.


Whether you’re a first-time visitor or a frequent traveler to Boston, this guide will help you make the most of your weekend trip. Join us as we take a deep dive into the city’s historical sites, provide recommendations for outdoor activities and entertainment, and give you insider tips on where to find the best local cuisine and unique shopping experiences. So, pack your bags and get ready to immerse yourself in the rich culture and vibrant spirit of Boston.


Exploring Historical Sites

Boston is a city steeped in history, and no visit would be complete without exploring its iconic historical sites. Start your journey with a visit to the Freedom Trail, a 2.5-mile long red-brick trail that takes you on a journey through the city’s revolutionary past. Along the trail, you’ll encounter historically significant sites such as the Massachusetts State House, Faneuil Hall, and the Old North Church.


One must-see stop along the Freedom Trail is the Paul Revere House. This 17th-century home was the residence of Paul Revere, a prominent figure in American history known for his midnight ride to warn of the approaching British troops. Step inside the house and walk in the footsteps of this legendary patriot.


Another historical gem is the USS Constitution Museum, located in the Charlestown Navy Yard. Get up close and personal with the world’s oldest commissioned warship afloat and learn about its rich history and legendary battles. Don’t forget to visit the Bunker Hill Monument nearby to commemorate the famous Battle of Bunker Hill.


For those interested in the darker side of history, a visit to the Salem Witch Museum is a must. Located just a short drive from Boston, this museum offers a fascinating insight into the infamous Salem witch trials of the late 1600s. Explore the exhibitions and learn about the hysteria that swept through the town during that dark period.


If you’re a book lover, be sure to visit the Boston Public Library, one of the oldest municipal libraries in the United States. Explore its grand architecture and vast collection of books, including rare manuscripts and first editions. Take a stroll through the beautiful courtyard, a hidden oasis in the heart of the city.


As you explore Boston’s historical sites, keep an eye out for the many statues and memorials scattered throughout the city. From the bronze statue of Benjamin Franklin in the heart of the city to the iconic statues of John Adams and John F. Kennedy in various locations, these tributes to important figures in American history add an extra layer of significance to your visit.


Immerse yourself in the rich history of Boston as you explore its historical sites. The city’s past comes alive as you walk the streets and visit these landmarks, offering a unique and memorable experience for history enthusiasts and curious travelers alike.


Visiting Museums and Galleries

Boston is renowned for its world-class museums and galleries, offering a diverse range of art, history, and culture to explore. Whether you’re an art aficionado or simply curious about different periods and styles, Boston’s museums will captivate and inspire you.


Start your museum-hopping adventure at the Museum of Fine Arts (MFA), one of the most prestigious art institutions in the country. With over 450,000 works of art spanning thousands of years, the MFA showcases masterpieces from renowned artists such as Monet, Van Gogh, and Rembrandt. From ancient Egyptian artifacts to contemporary installations, the museum offers a comprehensive journey through the world of art.


For a more modern and contemporary art experience, head to the Institute of Contemporary Art (ICA). Located on the waterfront, the ICA boasts a stunning architectural design that perfectly complements its cutting-edge exhibitions. Explore thought-provoking installations, innovative sculptures, and thought-provoking exhibitions by both emerging and established artists.


If you’re interested in history and science, don’t miss the Museum of Science. With interactive exhibits and engaging displays, this museum offers a hands-on learning experience for visitors of all ages. Discover the wonders of the natural world, explore space, and learn about groundbreaking scientific discoveries.


Boston is also home to the renowned Isabella Stewart Gardner Museum, a must-visit for art and architecture enthusiasts. Housed in an exquisitely designed building modeled after a 15th-century Venetian palace, the museum features an eclectic collection of European, Asian, and American art. Marvel at the lush indoor courtyard and immerse yourself in the beauty of this unique cultural gem.


Art lovers should also make a stop at the Museum of African American History, which celebrates the rich contributions and experiences of African Americans throughout history. Through thought-provoking exhibits and engaging storytelling, the museum sheds light on important events and figures, inviting visitors to explore and reflect upon the complex history of African Americans in the United States.


In addition to these iconic museums, Boston is home to numerous smaller galleries and art spaces, showcasing the works of local and emerging artists. Take a leisurely stroll through the SoWa Art + Design District in the South End or visit the vibrant galleries in the Fort Point neighborhood to discover contemporary art and support the local art community.


Immerse yourself in Boston’s vibrant art scene and explore the city’s museums and galleries. Whether you’re a seasoned art connoisseur or simply seeking inspiration and cultural enrichment, Boston’s artistic offerings will leave a lasting impression.


Enjoying Outdoor Activities

Boston’s charm extends beyond its historical sites and cultural institutions. The city offers a wealth of outdoor activities for nature lovers, adventure enthusiasts, and those seeking a breath of fresh air. From scenic parks to recreational areas, Boston provides ample opportunities to enjoy the great outdoors.


One of the best ways to appreciate Boston’s natural beauty is by exploring the Charles River Esplanade. This picturesque waterfront park stretches for three miles along the banks of the Charles River, offering stunning views of the city skyline and ample space for walking, jogging, or biking. Pack a picnic and relax on the grassy areas, or rent a kayak or paddleboard to explore the river.


If you’re looking for a peaceful retreat, head to the Arnold Arboretum, a 281-acre botanical garden located in the Jamaica Plain neighborhood. Stroll through the expansive grounds and immerse yourself in nature as you admire the diverse collection of trees, plants, and flowers. The arboretum also offers guided tours and educational programs for those who want to delve deeper into the world of horticulture.


Boston Common and the adjacent Public Garden are must-visit outdoor spaces in the city. As the oldest public park in the United States, Boston Common is steeped in history and offers a tranquil escape from the bustling city streets. Enjoy a leisurely walk, have a picnic, or simply sit on one of the park benches and people-watch. Just across the street, the Public Garden is known for its iconic Swan Boats, which have been delighting visitors since 1877.


For a taste of coastal beauty, head to the Boston Harbor Islands National and State Park. This collection of islands, accessible by ferry, offers a scenic escape from the city. Explore hiking trails, go camping, have a beach day, or take a guided tour to learn about the islands’ rich history and natural habitats.


Boston is also a city of sports lovers, and if you visit during the right season, catching a Red Sox baseball game at Fenway Park is a must. Experience the electric atmosphere of America’s oldest ballpark and cheer on the home team as you indulge in traditional ballpark treats like hot dogs and peanuts.


Outdoor enthusiasts will find plenty of opportunities for recreational activities along the Charles River. Rent a bike and cruise along the Charles River Bike Path, or lace up your running shoes and join the locals for a jog along the riverbanks. If you’re feeling adventurous, try your hand at sailing or paddleboarding with rentals available at various waterfront locations.


Whether you’re a nature lover, sports enthusiast, or simply seeking some fresh air and relaxation, Boston’s outdoor activities have something for everyone. Soak up the sunshine, enjoy the natural beauty, and make unforgettable memories in the city’s outdoor havens.


Sampling Local Cuisine

No trip to Boston is complete without indulging in its vibrant culinary scene. The city is renowned for its diverse range of food options, from traditional New England seafood to international flavors. Prepare your taste buds for a delightful journey through the tastes and aromas of Boston’s local cuisine.


When it comes to seafood, Boston has a reputation for serving some of the freshest and most delicious offerings. Head to the historic Quincy Market or the Seaport District to savor succulent lobster rolls, creamy clam chowder, and crispy fried clam strips. For a true New England experience, visit Legal Sea Foods, a local institution known for its top-notch seafood dishes and welcoming atmosphere.


For a taste of Boston’s Italian heritage, head to the North End neighborhood. This vibrant enclave is known for its authentic Italian eateries, charming bakeries, and gelato shops. Don’t miss out on a plate of homemade pasta, brick oven pizza, or a cannoli from one of the neighborhood’s iconic pastry shops.


Boston is also a city that celebrates farm-to-table dining. Visit the trendy neighborhoods of South End and Jamaica Plain to find restaurants that prioritize locally sourced ingredients and seasonally inspired menus. From innovative dishes to classic comfort food, these establishments offer a taste of Boston’s culinary creativity.


Don’t forget to try one of Boston’s most beloved treats: the Boston cream pie. This delectable dessert, consisting of layers of sponge cake, vanilla cream, and a chocolate ganache topping, is a true local favorite. Head to Omni Parker House, the birthplace of the Boston cream pie, or any of the city’s bakeries to experience the sweet delight.


If you’re a coffee lover, be sure to sample Boston’s burgeoning coffee scene. The city boasts a number of specialty coffee shops that serve up expertly crafted brews. From artisanal pour-overs to rich espresso-based beverages, you’ll find the perfect cup to fuel your exploration of the city.


Boston is also home to a thriving craft beer scene, with numerous breweries and taprooms scattered throughout the city. Take a brewery tour, sample a flight of locally brewed beers, and learn about the brewing process from the experts.


With its diverse culinary offerings and dedication to quality and innovation, Boston guarantees a memorable dining experience. Whether you’re a foodie looking for the next gastronomic delight or simply seeking hearty comfort food, Boston’s restaurants and eateries are sure to satisfy.


Shopping and Souvenirs

Exploring the vibrant shopping scene of Boston is a must-do to find unique keepsakes and souvenirs that will remind you of your visit to this lively city. From luxury boutiques and department stores to charming local shops, Boston offers a diverse range of retail experiences.


Newbury Street, located in the Back Bay neighborhood, is a shopping haven lined with high-end designer stores, trendy boutiques, and art galleries. Take a leisurely stroll down this charming street and browse through the latest fashion trends, jewelry, and home decor. This iconic shopping destination is also famous for its cafes and restaurants, offering the perfect spot to take a break and people-watch.


If you’re looking for something a little more unique, be sure to visit the SoWa Open Market in the South End. Held every Sunday from May to October, this outdoor market showcases local artisans, craftsmen, and food vendors. Discover one-of-a-kind handmade jewelry, artwork, clothing, and gourmet treats while enjoying live music and food trucks.


To immerse yourself in Boston’s literary history, a visit to the historic and independently owned bookstores is a must. Trident Booksellers & Cafe in the Back Bay area is a beloved spot for bookworms, offering a vast selection of books and a cozy cafe to enjoy a cup of coffee while you browse. Another notable bookstore is the Brattle Book Shop, one of the oldest and largest antiquarian bookstores in the country. Explore its collection of rare books and manuscripts or hunt for hidden treasures in its outdoor sale lot.


For a taste of Boston’s local art scene, head to the South End and visit the numerous art galleries that dot the neighborhood. Browse through contemporary artwork, paintings, sculptures, and photography, and even have a chance to meet local artists. Whether you’re looking to purchase artwork or simply appreciate the talent on display, the South End galleries offer a unique and enriching experience.


To find authentic Boston-themed souvenirs, make a stop at Blackstone’s of Beacon Hill. This charming boutique specializes in Boston-themed gifts, including apparel, housewares, jewelry, and locally made products. Pick up a “wicked awesome” Boston t-shirt, a mug adorned with the city skyline, or a handmade piece of pottery crafted by a local artisan.


Don’t forget to explore the lively Quincy Market at Faneuil Hall, a historic shopping center with over 100 shops and restaurants. Here, you’ll find a wide range of products, from apparel and accessories to gourmet food items and specialty goods. Sample local treats like Boston baked beans, cranberry jam, or indulge in a box of mouthwatering chocolates.


Whether you seek fashionable finds, literary treasures, local artwork, or Boston-themed souvenirs, the city’s diverse shopping options are sure to cater to your preferences. Explore the neighborhoods, take your time to discover hidden gems, and find the perfect memento to commemorate your trip to Boston.


Nightlife and Entertainment

When the sun sets in Boston, the city comes alive with a vibrant nightlife scene offering a wide array of entertainment options for visitors and locals alike. From live music venues and comedy clubs to trendy bars and dance clubs, Boston offers something for everyone to enjoy after dark.


If you’re a fan of live music, Boston’s music scene has you covered. The city boasts numerous venues that host concerts featuring a variety of genres. Head to the House of Blues in the Fenway neighborhood for big-name acts, or check out smaller venues like the Paradise Rock Club or the Middle East in Cambridge for a more intimate concert experience. From rock and pop to jazz and blues, Boston’s live music scene has something to suit every taste.


For a dose of laughter, visit one of Boston’s renowned comedy clubs. The Comedy Studio in Harvard Square has been a staple of the city’s comedy scene for over 20 years, featuring both established and up-and-coming comedians. Laugh Boston, located in the Seaport District, offers a modern and spacious setting for comedy shows that will have you in stitches.


Looking for a night of dancing and partying? Make your way to the lively neighborhoods of Fenway or Downtown Crossing, where you’ll find a variety of clubs and bars that cater to different music preferences and atmospheres. From hip-hop and EDM to Latin beats and retro hits, Boston’s dance clubs provide a vibrant and energetic nightlife experience.


If you prefer a more relaxed and low-key evening, Boston has plenty of cozy bars and pubs where you can unwind with a craft cocktail or local beer. The historic Cheers bar, made famous by the hit TV show, is a favorite among tourists. Alternatively, explore the craft beer scene at establishments like Trillium Brewing Company or Harpoon Brewery, which offer unique brews and a laid-back atmosphere.


For those seeking a more refined and sophisticated evening, Boston’s theater district is home to world-class theaters and performance venues. Enjoy a Broadway production at the Opera House or catch a show at the Wang Theatre. From musicals to plays, the theater scene in Boston will transport you into a world of captivating performances.


No discussion of Boston’s nightlife would be complete without mentioning its iconic Irish pubs. Step into establishments like The Black Rose or The Bebop and experience the warm hospitality and lively atmosphere of these traditional pubs. Enjoy a pint of Guinness, listen to live Irish music, and join the locals in a spirited sing-along.


As with any bustling city, it’s important to exercise caution and be aware of your surroundings when exploring the nightlife scene in Boston. Most venues have a cover charge or age restrictions, so be sure to check in advance and plan accordingly.


From live music and comedy to dancing and pub hopping, Boston’s nightlife and entertainment options guarantee endless fun and memorable experiences. So put on your dancing shoes, immerse yourself in the city’s vibrant energy, and create unforgettable nights in the heart of Boston.


Discovering the Boston Harbor

The Boston Harbor is not only a picturesque backdrop to the city but also a destination in itself. With its rich maritime history, stunning waterfront views, and a variety of activities, the harbor offers a unique and memorable experience for visitors.


A great way to explore the Boston Harbor is by taking a harbor cruise. Hop aboard a sightseeing boat or a historic schooner and sail along the harbor’s sparkling waters. Learn about the city’s maritime past, enjoy panoramic views of the skyline, and catch glimpses of iconic landmarks such as the Bunker Hill Monument and the USS Constitution.


If you’re looking for a more active experience, consider kayaking or paddleboarding in the harbor. Many rental companies offer equipment and guided tours, allowing you to explore the harbor at your own pace and get up close to the scenic islands and historic waterfront areas.


For a taste of the local seafood scene, visit one of the many restaurants and seafood shacks scattered along the waterfront. Treat yourself to a delicious lobster roll, fresh oysters, or a steamed clam feast while enjoying the ocean breeze and views of passing sailboats.


The Boston Harbor Islands National and State Park is a true gem of the harbor. Take a ferry from Long Wharf and spend a day or even a weekend exploring these 34 islands. Enjoy nature walks, swimming, picnic areas, and guided tours. You can even go camping on some of the islands, offering a unique opportunity to spend a night under the stars close to the city.


If you’re interested in maritime history, visit the Boston Tea Party Ships & Museum located on the Congress Street Bridge. Step back in time and relive the famous event that sparked the American Revolution. Participate in interactive exhibits, join in on reenactments, and even throw a crate of tea overboard!


Another historical landmark to explore is the Charlestown Navy Yard. Visit the USS Constitution Museum and get an up-close look at “Old Ironsides,” the oldest commissioned warship afloat in the world. Take a guided tour of the ship and learn about its role in American history.


For a unique vantage point of the harbor, visit the Institute of Contemporary Art (ICA) located on the waterfront. This contemporary art museum not only offers a diverse range of exhibitions but also has a stunning waterfront terrace where you can enjoy a drink while taking in the breathtaking harbor views.


Whether you choose to cruise, kayak, or simply relax by the water’s edge, the Boston Harbor provides a memorable experience. From its historical significance to its natural beauty, the harbor is a true gem of the city and invites you to discover its secrets and stories.


Relaxing in Parks and Gardens

When it comes to finding tranquility and green spaces in the bustling city of Boston, there are numerous parks and gardens that offer peaceful retreats for visitors and locals alike. Whether you’re looking for a serene spot for a picnic, a peaceful place to read a book, or a picturesque setting for a leisurely stroll, Boston has you covered.


One of the most iconic and beloved parks in Boston is the Boston Common. As the oldest public park in the United States, this 50-acre green space offers a respite from the urban hustle and bustle. Take a leisurely walk along its tree-lined paths, enjoy a paddleboat ride on the pond, or simply find a shady spot to relax and soak up the scenery.


Adjacent to Boston Common is the enchanting Public Garden, famous for its vibrant flower beds, meticulously maintained lawns, and serene Swan Boats. Take a leisurely stroll through the garden’s pathways, stop to admire the beautiful sculptures, or find a bench to sit and enjoy the peaceful atmosphere.


For a taste of Boston’s nature, head to the Arnold Arboretum, a 281-acre botanical garden located in the Jamaica Plain neighborhood. This picturesque park is filled with a diverse collection of trees, plants, and flowers, making it a perfect spot for nature lovers and those seeking a tranquil setting. Explore the winding paths, have a picnic on the rolling meadows, or simply sit and enjoy the beauty of your surroundings.


The Rose Kennedy Greenway is another gem of Boston’s green spaces. This linear park stretches through the heart of the city, with beautifully landscaped gardens, fountains, and art installations. Take a leisurely stroll along the park’s pathways, stop for a picnic, or relax on one of the park’s many benches while enjoying the views of the city skyline.


The Emerald Necklace is a series of interconnected parks and gardens that span approximately seven miles, creating a green oasis throughout the city. From the picturesque Jamaica Pond to the woodland trails of the Arnold Arboretum, the Emerald Necklace offers a variety of settings for relaxation and recreation.


For those looking to experience a unique rooftop oasis, the Prudential Skywalk Observatory offers stunning panoramic views of the city from its 50th floor. Enjoy the outdoor observation deck, where you can see the city’s skyline and beyond while feeling the breeze.


As you explore Boston’s parks and gardens, keep an eye out for seasonal events and activities that take place in these green spaces. From outdoor concerts and theater performances to yoga classes and art installations, there is always something happening to enhance the park experience.


Whether you’re seeking a peaceful retreat or a scenic setting for outdoor activities, Boston’s parks and gardens provide the ideal escape from the bustling city. Immerse yourself in nature, find solace in the serene surroundings, and create moments of relaxation and rejuvenation.


Recommended Day Trips

While Boston itself offers a plethora of attractions, there are also several delightful day trips you can take from the city to explore the surrounding area. From historic landmarks to picturesque coastal towns, these day trips provide a chance to discover even more of the beauty and charm that Massachusetts has to offer.


One of the most popular day trip destinations from Boston is Salem, known for its infamous witch trials in the late 1600s. Just a short drive from the city, Salem is home to several museums and historic sites that delve into the witchcraft hysteria of the past. Visit the Witch House, the only remaining structure with direct ties to the witch trials, or explore the Peabody Essex Museum, which showcases art and culture from around the world.


If you’re seeking a coastal getaway, head to Cape Cod and experience its quaint towns, picturesque lighthouses, and beautiful beaches. Enjoy a leisurely drive along the Cape Cod National Seashore, visit charming towns like Provincetown or Chatham, and indulge in fresh seafood at one of the many seaside restaurants.


A trip to Martha’s Vineyard is another must for nature lovers and relaxation seekers. This charming island, accessible by ferry from Cape Cod, is known for its pristine beaches, rolling farmland, and idyllic coastal towns. Rent a bicycle and explore the island’s quaint pathways, visit the famous Gingerbread Cottages in Oak Bluffs, and relax on the picturesque beaches.


For history buffs, a visit to Lexington and Concord will transport you back to the American Revolution. These neighboring towns played a crucial role in the fight for independence. Explore the Minute Man National Historical Park, witness the site of the Battle of Lexington, and visit the home of famous American writer, Louisa May Alcott.


For a charming New England experience, visit the town of Rockport on Cape Ann. Known for its picturesque harbor, quaint shops, and art galleries, Rockport offers a perfect combination of coastal beauty and artistic charm. Stroll along Bearskin Neck, admire the Motif No. 1, and savor the fresh seafood at one of the waterfront restaurants.


Lastly, for a dose of academic charm and history, visit Cambridge, the home of renowned universities, Harvard and MIT. Explore the historic Harvard Yard, stroll along the lively Harvard Square, and visit the Harvard Art Museums. Take a walk across the Charles River, and explore the MIT campus, known for its cutting-edge research and innovation.


These day trips from Boston offer a diverse range of experiences, allowing you to immerse yourself in history, enjoy the coastal beauty, and explore the charming towns of Massachusetts. Whether you’re interested in history, nature, or simply seeking a change of scenery, there’s a day trip from Boston that’s sure to satisfy your wanderlust.



With its rich history, vibrant cultural scene, and picturesque landscapes, Boston is a captivating destination for a weekend trip. From exploring historical sites along the Freedom Trail to immersing oneself in the world-class museums and galleries, Boston offers a multitude of experiences that cater to various interests and passions.


Outdoor enthusiasts will delight in the city’s parks, gardens, and the beautiful Boston Harbor. Relax in the serene green spaces, take a cruise along the harbor, or explore the charming neighborhoods that showcase the city’s unique character and charm.


Food lovers will be spoiled for choice in Boston, with its diverse culinary scene and delectable seafood offerings. Sample local delicacies, savor the flavors of the city’s renowned Italian cuisine, and treat yourself to Boston’s signature desserts.


As night falls, Boston’s vibrant nightlife comes alive. Enjoy live music performances, laugh at a comedy club, dance the night away at trendy clubs, or unwind in cozy bars and pubs. The city offers a range of options for every taste and preference.


For those looking to venture beyond the city’s boundaries, there are several recommended day trips that offer glimpses into the rich history, natural beauty, and coastal charm of Massachusetts. From Salem’s witch trial history to the scenic beauty of Cape Cod and Martha’s Vineyard, these day trips provide a chance to explore the surrounding area and create lasting memories.


In conclusion, a weekend trip to Boston is an opportunity to immerse yourself in the city’s unique blend of history, culture, and natural beauty. Whether you’re a history buff, an art enthusiast, a food lover, or simply seeking a getaway, Boston’s attractions and experiences are sure to leave a lasting impression. So pack your bags, embrace the spirit of adventure, and embark on a memorable journey through the vibrant streets of Boston.