If you’ve decided on a New England road trip, a day trip to Boston is a must. With centuries of history to discover, it might be a tough task, but it’s manageable! This guide will take you on a whirlwind adventure through one of America’s greatest cities. We’ll explore the Freedom Trail, hang on the USS Constitution, and dive into history in the Massachusetts capital, one of the most popular tourist destinations in the United States. So buckle up for the ultimate 24-hour Boston experience!
Wandering Boston on a Let’s Roam Scavenger Hunt
Wondering what to do on your day trip to Boston? There are plenty of options! Explore historical landmarks. Stroll through public parks and gardens. And most importantly, create lasting memories! We can help you do it all with your friends, coworkers, and loved ones on one of our 15 Boston hunts! Solve clues on a scavenger hunt, or get haunted on a ghost tour. Explore the best watering holes on a bar crawl, or indulge in an urban art walk! Whatever you choose, you’ll definitely experience the charm of Boston.
Starting the Day Off Right
Your Boston itinerary should begin with fueling up on the best breakfast around. When it comes to breakfast sandwiches in Boston, one name stands out: Mike & Patty’s! This spot holds the title of Boston’s highest-rated breakfast and sandwich shop, despite its humble beginnings. The original location is a cozy 175 square feet. It totally earns the nickname “Your Tiny Sandwich Shop.” In fact, it proudly claims to be the smallest eatery in the entire city of Boston!
The Freedom Trail
History buffs will marvel at Boston’s contribution to American history. To get the most out of this iconic city, we’re going to start by exploring some of the interesting historical sites on this 2.5-mile trail. While we won’t list them all, you can find a full list of sites on the Freedom Trail website.
Simply follow the trail’s metal seals and red bricks, and they’ll lead you to 16 must-see historic sites. The official starting point is Boston Common in the south. But for this itinerary, head over to the Charles River—we’ll begin at Bunker Hill instead. It just makes more sense when you’re short on time. After all, the southern sections of the trail offer a higher concentration of sightseeing opportunities. What’s even better is that by doing the route in reverse, you’ll end your day in Downtown Boston. That means you’ll be within arm’s reach of the city’s top-notch restaurants and bars, allowing you to wrap up your night in style. Soak up the vibrant atmosphere. Then treat yourself to some delectable cuisine and refreshing drinks as you reflect on the incredible history you’ve witnessed throughout the day!
What to Do on a Day Trip to Boston
Boston may be small compared to other major cities in the US. But that’s what makes it even better for a day trip. With this itinerary in hand, you can explore the city without breaking a sweat! You’ll hop from one awesome attraction to another with ease since we’ve organized them by location. No need to worry about getting lost or feeling like you’re running a marathon. Boston’s charm is packed into a compact space, so you’ll have more time to enjoy the sites, indulge in delicious food, and snap those envy-worthy Instagram shots. Plus, you’ll have plenty of opportunities to pop into cute shops, mingle with locals, and revel in the vibrant atmosphere that makes visiting Boston so special.
1. Catch a city view at the Bunker Hill Monument.
Situated in the charming neighborhood of Charlestown, the Bunker Hill Monument marks the northern end of the iconic Freedom Trail. This magnificent monument serves as a tribute to the Battle of Bunker Hill, a pivotal clash during the American Revolutionary War.
If you time it right, you might have the chance to ascend the 294 steps of the monument’s centerpiece obelisk. It’s worth the climb! From the top, you’ll be rewarded with breathtaking panoramic views of the Boston skyline and the picturesque Boston Harbor. It’s a sight you won’t want to miss!
2. Satisfy your inner sailor at the USS Constitution.
From the Bunker Hill Monument, take a delightful 15-minute stroll along the waterfront to reach the Charleston Navy Yard. This historic naval shipyard is home to a true American icon, the USS Constitution, fondly known as Old Ironsides. Dating back to 1797, this remarkable ship is one of the original warships of the US Navy. It holds the distinction of being the world’s oldest frigate that is still afloat.
Step aboard the USS Constitution, and embark on a fascinating tour guided by knowledgeable servicemen. You can gain insights into the ship’s weaponry, courageous crews, and thrilling naval adventures throughout history. Tours are available every 30 minutes from 10 a.m. to 5 p.m. daily, except on Mondays. Prepare to be transported back in time—the servicemen even dress in period attire during the tour! Don’t forget to explore the nearby USS Constitution Museum, open from Thursday to Sunday, for further insights into the ship’s captivating story.
If you’re in the mood to take things at a leisurely pace, take some time to wander through the Boston Historical Park and Charlestown Naval Shipyard Park, located in the vicinity. These peaceful green spaces offer a chance to unwind and absorb the historic surroundings. If you’re ready for more Freedom Trail adventures, head towards Boston’s vibrant North End neighborhood.
3. Take a quick stop at Copp’s Hill Burial Ground.
Once you cross the harbor, head down Hull Street. Within a couple of blocks, you’ll come across the fascinating Copp’s Hill Burying Ground. This historic cemetery, established way back in 1659, holds great significance and served as a crucial vantage point during the American Revolutionary War due to its location near the harbor. Legend says the Brits used the gravestones for target practice. Take a moment to appreciate its rich history and admire the views it offers over the glistening water. Though a quick stop, it’s a worthwhile opportunity to take in the stories of the more than 10,000 people who call Copp’s Hill their final resting place.
4. Visit the Old North Church.
As you continue east from the cemetery, you’ll discover the iconic Old North Church. This historic church, constructed in 1723, holds a significant place in American history: It was the starting point of Paul Revere’s legendary Midnight Ride to alert the patriots about the advancing British troops. On the way up, you’ll also spot a few lanterns. The lanterns are replicas of those used to send out the first warning signals during the Battle of Bunker Hill.
While the church’s interior may not boast extravagant ornamentation, it’s a must-visit for its remarkable historical significance. Don’t miss the opportunity to explore the bell-ringing chamber, which houses the oldest church bells in North America. These bells have witnessed centuries of events and still resonate with the echoes of the past. Step inside the Old North Church, learn the stories of patriots, and stand in awe of the enduring legacy that surrounds this hallowed place.
5. Visit the Paul Revere House.
A mere five-minute walk southeast from the church will lead you to the remarkable Paul Revere House, a must-visit historical site in Boston. This Colonial-era home holds great significance as it served as Paul Revere’s primary residence from 1770 to 1800. History enthusiasts will delight in taking a guided tour of the house. You can gain valuable insights into 18th-century life in New England and discover the fascinating details of Revere’s renowned midnight ride. As you explore the rooms, you’ll come across intriguing artifacts that provide a glimpse into Revere’s business ventures. They all add to the allure of the experience!
6. Explore the North End Neighborhood.
Affectionately known as Little Italy, the North End is a vibrant and captivating neighborhood that holds a special place in the heart of the city. The North End is brimming with an abundance of fantastic Italian restaurants, pastry shops, cozy cafes, and inviting delis. It’s a true food lover’s paradise! If you’re starving, North End is a good place to grab lunch. If not, just wander a bit, soak up the atmosphere, and save your hunger for Quincy Market!
7. Fuel up at Quincy Market in Faneuil Hall Marketplace.
From the historic Paul Revere House, follow the charming North Street southwards, and cross over the delightful Rose Kennedy Greenway. In less than ten minutes, you’ll stumble upon your next destination on your action-packed 24-hour Boston adventure—the iconic Faneuil Hall Marketplace.
Get a bite to eat!
While you explore the endless vendors of Faneuil Hall Marketplace, be sure to carve out some time to indulge in a delectable meal at Quincy Market. Located just behind the meeting hall, Quincy Market Food Colonnade boasts 25 Bostonian restaurants and food vendors, offering a wide array of culinary delights. Chow down on New England favorites such as creamy clam chowder and scrumptious lobster rolls. Getting a few small dishes from an assortment of vendors is the perfect way to immerse yourself in the authentic flavors of Boston.
After satisfying your taste buds, take a leisurely stroll through the rest of the marketplace. Both the North Market and South Market buildings house an eclectic mix of shops, offering everything from unique souvenirs and stylish fashion accessories to delightful home decor and practical luggage. It’s a shopper’s paradise! You can find a little something for everyone.
Enjoy the vibrant atmosphere.
The squares near Quincy Market and Faneuil Hall come alive with world-class street performers who are sure to captivate your attention. You never know what extraordinary talents you might encounter, from awe-inspiring sword jugglers to mind-bending contortionists and even mesmerizing escape artists. It’s a delightful spectacle that adds an extra layer of excitement to your Boston adventure.
8. Visit historic Faneuil Hall.
If you’re a history enthusiast, don’t miss the opportunity to visit Faneuil Hall itself. Make your way up to the second floor, and step into The Great Hall, a treasure trove of fascinating artifacts from the era of Independence. Take some time to explore and appreciate the remarkable collection on display. Faneuil Hall played a pivotal role in Boston’s history as a venue for influential speeches advocating for American independence. Some of the great orators who graced its stage include Samuel Adams, one of the Founding Fathers, and esteemed abolitionist Frederick Douglass. Soak in the atmosphere, and imagine the impassioned words that once echoed through these historic walls.
9. Roam around Boston’s Market District.
After immersing yourself in the historic charm of Faneuil Hall, take a delightful detour north into Boston’s Market District. This picturesque area, with its roots dating back to the 19th century, is a haven for photography enthusiasts and history lovers alike. Lose yourself in the winding cobblestone streets as you admire the splendid architecture that spans the 18th and 19th centuries. The elegant buildings create a captivating contrast to the modern skyscrapers of the nearby Financial District, just a few blocks south.
As you wander, you may find yourself yearning for a refreshing beverage. Look no further than Bell in Hand Tavern on Union Street. This beloved pub, which opened its doors in 1795, proudly claims the title of the oldest public house in the United States. Step inside, raise a pint, and savor the historic ambiance that has been enjoyed by countless patrons over the centuries.
If you’re still craving an afternoon snack, taste Boston’s renowned seafood at Union Oyster House, one of the oldest restaurants in America. Indulge in a bowl of divine clam chowder, or treat yourself to a mouthwatering lobster roll.
10. Step into colonial history at Old State House.
As you continue your journey along the Freedom Trail, make your way south from the Market District, and within a leisurely ten-minute stroll, you’ll arrive at the Old State House. Let your imagination take you on a journey back in time. This magnificent building, originally known as the Town House, witnessed some of the most dramatic events of the Revolution in Massachusetts. Imagine standing in the very spot where history unfolded, where the pulse of colonial government began to beat. In 1713, when it was first constructed, the Old State House served as the hub of royal authority in the Massachusetts Bay colony. But its balcony soon became a pulpit for Revolutionary orations, including the first reading of the Declaration of Independence. It’s also the site of the Boston Massacre.
11. Take in the Old South Meeting House.
Walk a little farther to the awe-inspiring Old South Meeting House. This magnificent architectural gem, constructed in 1729, proudly stands as a National Historic Landmark. During colonial times, the Old South Meeting House was the largest building in the city. It played a pivotal role in shaping the destiny of the colonies. It was within these hallowed walls that numerous protests were organized, sparking the flames of independence. Notably, it was here that the Sons of Liberty, a group of passionate revolutionaries, orchestrated the infamous Boston Tea Party, an act that reverberated throughout history.
Today, the Old South Meeting House stands as a testament to the courage and determination of those who fought for freedom from British rule. Step inside this remarkable museum, and you’ll be transported back in time, feeling the presence of the great individuals who paved the way for America’s independence. Take your time to explore the exhibits, immerse yourself in the interactive displays, and soak in the rich history that surrounds you. The Old South Meeting House is not just a museum; it’s a living testament to the indomitable spirit of the American people.
12. Head down to the Boston Tea Party Ships & Museum.
The Boston Tea Party Ships & Museum is an 11-minute walk from the Old South Meeting House and was voted the best patriotic attraction. You’ll truly feel like you’re in 1773 as you embark on a captivating tour of the Boston Tea Party Ships & Museum.
As you journey through the museum, you’ll gain a deeper understanding of the political climate surrounding the Tea Act imposed by the British Parliament. Through innovative 3D holograms and the passionate portrayal of live actors, you’ll be transported to the heart of the action. Experience the exhilaration of being a member of the “Sons of Liberty” as you witness the historic Boston Tea Party unfold before your eyes. The tour doesn’t stop at mere observation. You get in on the action and participate in throwing tea overboard, just as the Patriots did all those years ago. Feel the adrenaline and sense of defiance as you make your mark on history.
The tours typically last a little over an hour and commence every 15 minutes, with the exception of the fall and winter seasons when they start every 30 minutes. If you’re planning a visit during these times, it’s advisable to account for the adjusted schedule and allow for extra time to fully embrace this engaging journey.
13. Converse with locals and travelers at Boston Common.
Prepare to wrap up your Freedom Trail adventure at the iconic Boston Common, the official starting point of this historic trail. Spread across 50 acres, this park holds the distinction of being not only Boston’s but also the United States’ oldest public park, established in 1634. Its rich history is as captivating as its sprawling green landscapes. If you have kiddos in tow or you’re just feeling young at heart, you can also take a few minutes to ride the vintage carousel!
Throughout the years, Boston Common has witnessed significant public gatherings, attracting legendary figures like Pope John II, Gloria Steinem, and Martin Luther King, Jr. It has played a pivotal role in the city’s narrative, serving as the encampment for British troops prior to the American Revolution. Today, it continues to be a vibrant hub where visitors and locals gather to enjoy picnics, engage in sports, or simply take a leisurely stroll amidst its picturesque scenery.
As you make your way to the park, don’t miss the chance to explore the Granary Burying Ground, a cemetery dating back to 1660. It’s the final resting place of notable historical figures such as Samuel Adams, John Hancock, and Paul Revere and reminds us of their enduring contributions to American history.
Adjacent to the burial ground stands the remarkable Park Street Church, a venerable evangelical church that has stood since 1804. Its impressive structure and rich heritage make it a noteworthy stop on your journey. To this day, the church draws a devoted congregation of over 2,000 worshippers each week.
14. Take a boat ride in Boston Public Garden.
As you wrap up your exploration of Boston Common, make your way westward across Charles Street to the enchanting Boston Public Garden. Established in 1837, this picturesque park is a delightful oasis in the heart of the city. For an added touch of tranquility and whimsy, treat yourself to a leisurely boat ride on the iconic Swan Boats. Drift along the tranquil waters, surrounded by the beauty of the garden and the graceful presence of the swans. It’s a quintessential Boston experience that promises relaxation and a unique perspective of the park.
15. Roam the streets of Beacon Hill.
Nestled just north of Boston Common, the enchanting neighborhood of Beacon Hill awaits. Stepping into this historic district feels like a journey back in time, with its timeless allure and rich architectural treasures. Dating back to the late 18th century, Beacon Hill exudes a refined elegance that captivates visitors.
Take a stroll through the picturesque streets, and be mesmerized by the graceful rowhouses adorned with intricate craftsmanship. As you wander along Beacon Street and Acorn Street, be sure to pause and appreciate the meticulously designed doors that add a touch of charm to each residence. The neighborhood’s beauty is a testament to its storied past.
16. Tour the Massachusetts State House.
If you find yourself with some extra time in the Beacon Hill Historic District, don’t miss the opportunity to embark on a captivating walking tour of the Massachusetts State House. Allow approximately 45 minutes to delve into the rich history and marvel at the architectural splendor of this iconic building, boasting its renowned copper dome.
The 1790s-era Massachusetts State House is considered one of Boston’s finest architectural gems. Join one of the free guided tours, led by knowledgeable guides, and immerse yourself in the fascinating stories and significance behind this historical landmark. Departing from the Doric Hall, these tours are available daily from 10:00 a.m. to 3:30 p.m.
17. Admire the views at Copley Square in Back Bay.
A walk from Beacon Hill will lead you to the vibrant Copley Square in the Back Bay District, a journey taking approximately 20 to 25 minutes. As you arrive, you’ll be captivated by the juxtaposition of Boston’s historic and modern architecture that grace this charming city square, dating back to the 19th century.
Within Copley Square, a true gem awaits—the awe-inspiring Trinity Church. Erected in 1877, this majestic example of Romanesque Revival architecture demands a moment of admiration. Step inside Trinity Church, and be enchanted by the intricate stained-glass windows and magnificent organs, which add to the church’s splendor.
18. Shop for the latest fashions on Newbury Street.
Just a short two-block walk north of Copley Square awaits Newbury Street, Downtown Boston’s premier shopping destination. This bustling street is a shopaholic’s paradise, boasting a plethora of luxurious boutiques, charming eateries, stylish salons, and indulgent spas. Together with nearby Commonwealth Avenue, it forms one of the city’s most esteemed and coveted stretches.
19. Enjoy a delicious dinner in the Seaport District.
As your eventful 24-hour tour of Boston comes to a close, make your way to the vibrant Seaport District in South Boston. This former industrial area has undergone a remarkable transformation and has become one of the city’s trendiest neighborhoods. With its array of hip restaurants, rooftop bars, and stylish hotels offering stunning views of Boston Harbor, the Seaport District is the perfect place to end your day.
If you’re seeking an authentic taste of Boston cuisine, make sure to visit Legal Sea Foods Harborside. This sought-after location of the popular local chain is a must-visit. Indulge in a casual seafood dinner on the first floor, where you’ll have a wide selection of mouthwatering dishes to choose from. Options include delectable offerings such as Portuguese seafood stew, classic clam chowder, white clam pizza, and the flavorful Poor Man’s Surf and Turf. Be sure to save room for the iconic Boston cream pie for a truly satisfying end to your Boston cuisine experience. After savoring your meal, make your way to Legal’s relaxed rooftop bar, where you can unwind with refreshing cocktails while enjoying beautiful views of Boston Harbor.
20. Enjoy Boston’s nightlife.
If you still have some energy, it’s time to explore Boston by night! Let’s head for Back Bay. This lively neighborhood is full of trendy dance clubs, historic Irish pubs, and old-fashioned taverns. Enjoy a spicy margarita in an underground club, or grab a good book at Bukowski’s!
While you can certainly explore Boston’s nightlife on your own, if you want a little organization and added fun, check out our “Back Bay Beat Bar Crawl.” We’ll take you on a fun-filled adventure of trivia and photo/video challenges as we explore four of Boston’s best watering holes. If you’re traveling to Boston with your besties or your boo, we can’t think of a better way to cap off the night. You’ll laugh, dance, drink, and finish your day trip to Boston in style!
With this travel guide in hand, you’re now prepared for one of the best day trips in the USA. A day trip to Boston following the iconic Freedom Trail has something for every kind of traveler. From indulging in delicious seafood and exploring charming neighborhoods to visiting historic buildings and getting in some excellent shopping, you’ll truly soak up the essence of Boston. If you still have time on your getaway, take a tour of Fenway Park, home of the Red Sox, check out the Museum of Fine Arts, or take a tour of Harvard University.
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