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Boston Historic Sites

Must See Boston Landmarks Guide for Your Vacation

Boston, a city steeped in historical charm and modern innovation, is a must-visit destination for discerning travelers. This vibrant metropolis is a treasure trove of iconic landmarks, from the cobblestone streets of the Freedom Trail to the hallowed halls of Harvard University. Whether you’re a history buff, a foodie, or simply a curious explorer, Boston’s eclectic mix of attractions provides countless opportunities for discovery.

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Romantic Things To Do in Boston on a Date

The cobblestone streets, beautiful parks and historic buildings of the Cradle of Liberty set the perfect backdrop to celebrate a budding or long-term romantic relationship. Boston features a number of romantic things to do. Whether you are heading out to celebrate an anniversary, Valentine’s Day or just the perfect Boston date night, you can choose from simple pleasures or extravagant adventures. Locals as well as visitors can experience unforgettable outings with one of the following romantic things to do in Boston.

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JFK Museum

Designed by I.M. Pei, the John F. Kennedy Library was dedicated by President Jimmy Carter and the Kennedy Family in 1979. Located on a ten acre park, the museum is dedicated to the life and legacy of the 35th president of the United States. The library also hosts the Profiles in Courage award, given annually to honor elected public officials.

Things to Do Near Copley Square Boston

Named to honor the famed Boston artist John Singleton Copley, this Back Bay neighborhood is well known for its history and iconic architectural structures. Here, you can spend the day enjoying its charms in the way of various cafes, historical points of interest and upscale shops. There is also much to do, see and explore just footsteps away. Here’s a guide to some of the top things to do near Copley Square.

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Boston Field Trip Tours

Our Historical Tour is geared to all ages and takes you through Boston while recounting the history of our beautiful city. Your conductor will tell stories from the past while weaving in current events and happenings as well by mixing the old and the new.

Our Sons and Daughters of Liberty Tour is geared toward middle school students and focuses on The Revolutionary War time and history. It is an interactive tour with a costumed character on board and two stops along the way.

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Beacon Hill / Antique Row

6 Stop 6

One of Boston’s oldest neighborhoods, Beacon Hill is known for its charming, narrow cobblestone streets, federal style row houses and gaslit street lamps. It’s also considered to be one of Boston’s most desirable and expensive residential areas in the city. A visit to Boston isn’t complete without a stop here. Whether to shop, dine or wander about admiring the architecture and numerous historic sites, there are so many things to do in Beacon Hill.

Old State House

5 Stop 5

The Old State House, built in 1713 on the site of the first Town House, is the oldest surviving public building in Boston. The building served as a meeting place for the exchange of economic and local news and was said to be the center of politics in the colonies. The Declaration of Independence was read from the balcony on the east side of the building, and just below it is the spot where the Boston Massacre took place. The Old State House is one of the most important public buildings in the U.S.

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Historic North End

2 Stop 2

Welcome to Boston’s Little Italy. The North End is famous for the many authentic Italian restaurants, cafés, espresso bars, and sandwich shops that dot the neighborhood. The area features nearly 100 restaurants, ranging from the authentic Italian and Italian-American family style to Chinese, Thai, and local seafood. After dinner, stop by one of the world famous pastry shops. Mike’s Pastry and Modern Pastry each have their own unique twist on classic desserts. Get there early to avoid the lines!

Bunker Hill Monument

3 Stop 3

The Bunker Hill Monument was the first public obelisk in the United States designed to commemorate the Battle of Bunker Hill. The battle was actually misnamed because the majority of the action took place on Breed’s Hill and that is where the monument sits. The monument was begun in 1827 but construction had to be halted and it wasn’t completed until 1843. The architect, Solomon Willard, had the granite for the 221 ft structure brought in from Quincy, Massachusetts.

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Getting Around Boston On Vacation

open all day

When planning your Boston vacation, keep in mind that while the city is compact and easy to get around, driving your own car is not highly recommended. The streets and neighborhoods can be jumbled and difficult to navigate, especially if you’re not familiar with them. Between the many one-way streets and the confusing layout, you could spend lots of your precious vacation time getting lost and turned around. Read on for some of the top options to get around Boston.

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Must Do Activities For First Time Visitors To Boston

The city of Boston is filled with things to do from visiting popular museums to walking the Freedom Trail. Enjoy Boston’s rich history and see all the sights during your trip. After touring the major attractions, take a leisurely stroll around the Boston Public Garden or stop by for a refreshing drink at Cheers. Conveniently located near the trolley stops, these attractions are must-dos for first time visitors of all ages.

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Things to Do in the Winter

When the temperature starts to drop and the winter season begins, there’s still plenty of fun to be had in Boston. Whether visiting many of the city’s most popular indoor attractions or enjoying events and other seasonal activities, here are some of the top things to do during winter in Boston.

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Things to Do in Boston During the Spring

Spring is in the air! And you know what that means – warm days filled with sunshine, inviting you to get out and enjoy all there is to do and see in Boston. Read on for some of the top things to do in Boston during spring. Take a Ride on a Swan Boat
. Nothing says “welcome spring!” like the opening of the Swan Boats at the Boston Public Garden. It has been more than 130 years since the Swan Boats made their first voyage on the beautiful waters of the lagoon. This family-owned business has been welcoming guests for generations and is one of the city’s most unique and beloved traditions.

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Things To Do With Kids

If you’re heading to Boston with family, great fun is in store for everyone. The Cradle of Liberty is a wondrous place where old and new mesh beautifully and history and culture abound on every corner. There are a ton of things to do with kids including attractions, sights, museums, and activities throughout Boston. Looking for the most efficient and entertaining way to visit many of the things to do in Boston with kids? Look no further because Old Town Trolley Tours offers parents a relaxing way to tour all the best attractions in Boston for kids. Parents don’t have to worry about searching for directions to the New England Aquarium, driving to the Museum of Science, or finding parking while traveling from all of Boston’s best attractions. Our hop on and hop off trolley tours allow the parents to concentrate on having fun with their kids instead of worrying about logistics. There are so many awesome things to do with kids in Boston!

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Labor Day in Boston

Residents of Boston typically flee the city during the Labor Day Weekend to Cape Cod and Martha’s Vineyard for the last holiday celebration of the summer. This makes it a great time for vacationers to visit Boston with less traffic and easier access to the attractions. Check out some of the things to do in Boston during Labor Day weekend:

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How To See Boston in 2 Days

Your friends who have traveled here might say you need more than 2 days in Boston to see all the best attractions, but many of the attractions only require 30 minutes to an hour for a tour. This means that you can easily visit five Boston attractions per day and still have time for three leisurely meals; and we all know how important it is to eat the great food in Boston! Here’s a recommended itinerary from our travel planners who know all the shortcuts.

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How to See Boston in 1 Day

The city of Boston is one of the most visited destinations in the country and with good reason. Millions of people come each year to experience the rich heritage that comes alive on practically every corner, the abundance of cultural attractions, entertaining venues and diverse dining scene. If you only have one day to explore Boston, jump on the Old Town Trolley and follow these recommended stops to see the best of the city.

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Granary Burying Ground

13 Stop 13

Founded in 1660, the Granary Burying Ground is the third oldest burying ground in Boston. During the Revolution, the area where the Park Street Church now stands had been used to hold grain, which is the reason for the burying ground’s name. Located on Tremont Street, the following famous individuals are buried in the Granary Burying Grounds: Peter Faneuil, Sam Adams, Crispus Attacks, John Hancock, James Otis, Robert Treat Paine, Paul Revere, and members of Ben Franklin’s family.

African Meeting House

13 Stop 13

Dedicated in 1806, the African Meeting House is the Oldest African American Church and was the First African Baptist Church in the United States. Over the years it also served as a school and a community meeting place. It was here that William Lloyd Garrison founded the New England Slavery Society, making it the center of the abolitionist movement. In 1972, the building was acquired by the Museum of Afro-American History and it was restored in 1987. Today, the museum commemorates African American history from slavery to the abolitionist movement, with a focus on educational equality.

Black Heritage Trail

13 Stop 13 open Mon-Sun

The Black Heritage Trail features various homes, memorials, and sites that are significant in the history of Boston’s 19th century African American community. The first slaves arrived in 1638 and by 1705 there were over 400. At this time there were also the beginnings of a free black community in the North End, and by 1790, the time of the first census, Massachusetts reported no slaves. The trail includes the Robert Gould Shaw & the 54th Regiment Memorial, first black regiment, the George Middleton House, the oldest home built by African Americans on Beacon Hill, and the Phillips School, one of Boston’s first schools with an interracial student body.

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Kings Chapel & Burying Ground

5 Stop 5

Kings Chapel is a Christian Unitarian church located on Tremont and School Streets. The church was organized in 1686 as an Anglican Church. In 1785 it became the oldest member of the Unitarian Universalist Association and the first Anglican Church. Beside the church is the Kings Chapel Burying Ground, which was Boston’s only burial ground for 30 years. Many historical figures are buried here, including John Winthrop, the colony governor, William Dawes, who rode with Paul Revere on the Midnight Ride, Mary Chilton, the first woman off the Mayflower, and William Emerson, Ralph Waldo Emerson’s father. The original building was a wooden church built in 1688 and it was replaced by the current stone building in 1754. The bell was hung in 1772 and was recast by Paul Revere in 1814; it still rings at services today.

Massachusetts State House

13 Stop 13

In the distinctive gold-domed building atop Beacon Hill, the past meets the present. On weekdays, you can discover Massachusetts’ history on a free tour of the center of the state government. The building, completed in 1798, was designed by Charles Bulfinch to replace the Old State House.

In addition to housing the state government, the State House also displays various portraits of governors, murals depicting the state’s heritage, and statues inside and on its grounds. The building is recognizable because of its dome sheathed in copper and covered by 23 karat gold, as seen in the film The Departed.

Trinity Church

11 Stop 11

Boston’s Trinity Church was founded in 1733 and was originally located in downtown Boston. After the Great Boston Fire of 1872, the church complex moved to its current location and construction was completed in 1877. The impressive church was designed by Henry Hobson Richardson and is the first instance of the Richardsonian Romanesque style. Trinity Church is a Boston landmark and a cultural center for the city.

Copley Place

10 Stop 10

Copley Square, named after the American portraitist John Singleton Copley, is a historic focal point of this busy commercial area. A bronze statue of Copley can be found on the northern side of the square. Nearby Boylston Street offers shopping and attractions plus Newbury Street features upscale boutiques and restaurants in its quaint 19th century townhouses.

Boston Athenaeum

13 Stop 13

One of the oldest libraries in the United States, the Athenaeum was founded in 1807 and is an exclusive club of sorts in which a membership is required to use the many magnificent resources of this institution. But feel free to visit the first floor of this historic building that is open to the public and is home to an art gallery with a variety of rotating exhibits. Marble busts, porcelain vases, oil paintings, books and more are a delight to browse through and view. There’s also a children’s room with cozy reading nooks that overlook the Granary Burying Ground.

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Charles Street Meeting House

6 Stop 6

The Charles Street Meeting House in Beacon Hill is a historic church that was built in 1807. Its first congregation was the Third Baptist Church, which baptized its members in the Charles River. Before the Civil War, the church was an important site for the anti-slavery movement, used for speeches by Frederick Douglass, William Lloyd Garrison, Harriet Tubman, and Sojourner Truth. The building is currently used for commercial purposes.

Christian Science Plaza

9 Stop 9

The Christian Science Plaza is the location of the First Church of Christ, Scientist, one of the largest churches in New England. The plaza consists of 14 spacious and serene acres, paved in brick and granite, with orderly rows of trees, buildings, stone benches, a large reflecting pool and a circular fountain. The Mother Church, built in 1894, consists of a Romanesque Church Edifice with a bell tower and stained glass windows, and the larger Church Extension, added in 1906, is a mix of Renaissance and Byzantine architecture.

USS Constitution and Museum

3 Stop 3 open Closed on Mondays during the off season.

Launched in 1797, the USS Constitution is the oldest commissioned warship still afloat. Crisscrossing the globe, this three-masted frigate participated in the Barbary War off the coast of North Africa and sailed the Caribbean in search of pirates. She earned her nom de guerre Old Ironsides during the War of 1812 when enemy cannonballs bounced off her resilient wooden hull. Docked in the Charlestown Navy Yard, the famous ship is a floating museum open to public. It is also a stop on the on the Freedom Trail and the Old Town Trolley.

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Copp’s Hill Burying Ground

2 Stop 2

The gravestones in Copp’s Hill Burying Ground, Boston’s second oldest burying ground, tell the story of the population of the North End in colonial times. Originally known as Windmill Hill, the hill took the name of William Copp, a shoemaker who donated the land for a burying ground in 1659. It is the place of rest for thousands of artisans, craftspeople, and merchants. Some of the well known individuals are Increase and Cotton Mather, of the family of ministers, Robert Newman, sexton of the Old North Church at the time of Paul Revere’s ride, Edmund Hart, shipyard owner and builder of the USS Constitution, and Shem Drowne, the artist who made the weathervane for Faneuil Hall, among others.

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Old North Church

2 Stop 2

Officially called Christ Church, the Old North Church is the oldest church building in Boston, a National Historic Landmark, and a stop on the Freedom Trail. Built in 1723, the Old North Church was inspired by the works of Christopher Wren, a British architect. It is most commonly known as the first stop on Paul Revere’s “Midnight Ride,” where he instructed three Boston Patriots to hang two lanterns in the church’s steeple. The lanterns were used to inform Charlestown Patriots that the British were approaching by sea and not by land.

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Boston Massacre Site

5 Stop 5

On March 5, 1770, the tension from the British military occupation of Boston escalated into the event now referred to as the Boston Massacre. There was heavy military presence in downtown Boston in order to maintain control over civilians and to enforce the Townshend Act. Various brawls between soldiers and civilians had taken place; but the evening of March 5th was the first to result in civilian deaths. Today the site of the massacre is marked by a cobblestone ring on the traffic island at the intersection of Devonshire and State Streets.

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Faneuil Hall

1 Stop 1 (617) 426-6500 open 7 Days a Week

One of Boston’s most well known historic sites, Faneuil Hall Marketplace was constructed in 1742 and served as a marketplace and meeting hall since it first opened its doors. Named after the wealthy merchant who provided funding for the hall, Peter Faneuil, this significant structure has been the site of many important and inspirational speeches by famed Americans, including Samuel Adams. When visiting Boston, a stop here is definitely a must do.

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FAQs

Our Boston tour is 13 miles long and two hours from start to finish, but our route is designed for you to hop off at any stop, explore a Boston attraction or neighborhood, and hop back on when you are ready to resume your Boston sightseeing experience.

You may start your Old Town Trolley Tour at any of our convenient stops. Click on Map and Stops to see a list of our stops with information about the attractions and points of interest at each stop.

The tour visits South End, Back Bay, Historic North End, Beacon Hill, the Theater District, Downtown Crossing, the Seaport District, and Charlestown.

We operate the city’s largest fleet of sightseeing vehicles and this allows us to pick up and drop off more frequently than any other tour company. The frequency of the trolleys depends on the time of the year, traffic, and weather conditions, but typically it is every 20 minutes. April – October: Daily. 9am – 5pm. November – March: Daily. 9am – 4pm.

The Freedom Trail is a 2.5-mile urban brick walking path that takes in different historical Boston sites. The trolley tour gets you close to many of the sites along the Freedom Trail, as well as all the other major points of interest around the city of Boston. Our Boston tours help you explore the entire Freedom Trail without having to walk it all on foot.

If you’ve ever visited or plan to visit Boston, you’ll know that getting around can be a bit tricky. However, there’s an easy solution to that — the Old Town Trolley. Hop on, and you’ll be able to explore some of the city’s best attractions without the bother of driving or navigating traffic. Exploring Boston without a car is easier than you think thanks to Old Town Trolley. From historic sites and shopping to amazing food and beautiful beaches, Boston has something for everyone, and the trolley takes you to all the best spots.

Boston’s most picturesque neighborhood is Beacon Hill, an area that boasts stunning architecture, cobblestone streets, and charming boutiques. For those who want to make the most of their time and see Beacon Hill from a unique perspective, hopping on the Old Town Trolley is the way to go.

The first stop of the Old Town Trolley in Beacon Hill is at the Massachusetts State House. From this towering location, visitors can take in the stunning panoramic views of the city and the Charles River. The tour guide will provide visitors with fascinating facts about the State House’s history, including the famous codfish atop its dome, the symbol of Boston’s fishing industry.

The trolley then takes visitors through the heart of Beacon Hill’s residential area, a place filled with old brick houses, antique gas lamps, and postcard-perfect scenery.

Continuing down Beacon Hill, the trolley stops at the legendary Cheers bar, also known as the set of the hit TV show, “Cheers.” Visitors can sit at the same bar where Norman and Cliff once did, take photos, and enjoy the historic décor.

Boston’s Beacon Hill is a hidden treasure of American history, and the Old Town Trolley is the perfect way to experience it. From the State House’s panoramic views to the blue skies to stopping at a bar where everyone knows your name, this tour offers visitors a unique way to see the city’s hidden treasures while learning about Boston’s vibrant past.

Here are some of the must-see attractions that you can explore on the Old Town Trolley Tour:

1. The Freedom Trail: This iconic 2.5-mile-long trail takes you through 16 significant historical sites that were crucial to the American Revolution. You’ll see the Massachusetts State House, Paul Revere’s House, Old North Church, the USS Constitution Museum, and more. The Freedom Trail is a fascinating way to learn about the city’s rich history.

2. Acorn Street: Located in Beacon Hill, this street is a throwback to Colonial times with its cobblestone streets, gas lamps, and impeccably preserved 19th-century homes. Its houses are some of the oldest in Boston, and their exteriors have remained mostly unchanged for over a century. Acorn Street’s timeless look and feel, mixed with its New England charm, has made it a favorite among filmmakers.

3. Boston Tea Party Ships & Museum: The Boston Tea Party Ships & Museum is an interactive, high-tech, floating museum. Unlike anything you’ve ever experienced before, this unique museum sits on a barge in the water and includes tours on restored tea ships and a stunning, interactive documentary that immerses you into the events that led up to the American Revolution.

4. Quincy Market: This colorful marketplace is a shopper’s paradise, with more than 100 vendors selling everything from souvenirs to food. You can indulge in some classic Boston dishes such as clam chowder or a lobster roll.

5. Bunker Hill Monument: This 221-foot granite obelisk commemorates the Battle of Bunker Hill, which was a pivotal moment in the American Revolution. You can climb to the top for a stunning view of the city.

Boston transforms into a picturesque and vibrant city at night, and it offers plenty of things to do for those who are up for some nighttime fun. If you’re visiting Boston this summer, there’s no better way to explore the city after dusk than taking the Boston Summer Night Tour by Old Town Trolley. You’ll be able to visit historic landmarks and hidden gems that are illuminated by the city’s glow. From the Old North Church and the USS Constitution, Boston has a plethora of iconic and historic landmarks to explore. From the stunning harbor views to the twinkling skyline at night, explore these sites under the cover of darkness, where the ambiance and atmosphere are simply magical.

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