120 Fun Things To Do in Boston

1. 120 Fun Things to do in the Heart of Boston
Cotting School is currently located in Lexington, but from 1893 to 1988 our school was located in the heart of Boston. So,
in celebration of our 120th
year, here are 120 fun things to do in Boston. Please let us know when you’ve competed the
list! We would love to hear which locations you enjoyed.
Dave Manzo
1. Visit 241 St. Botolph Street, Cotting’s home (cotting.org/history) from 1904 to
1988 and see the plaque commemorating the founding of the school.
2. Visit the Boston YMCA at 316 Huntington Ave, where the Cotting Falcons
Basketball Team once played with Celtic legend Larry Bird. This was the first
“Y” in America.
3. Visit Boston Symphony Hall (www.bso.org) at 301 Massachusetts Ave. Here
on June 30, 1930, Rear Admiral Richard Evelyn Bird raised money for
Cotting School by describing his flight to the South Pole.
4. Stop at the Mapparium, at the Christian Science Center at 200
Massachusetts Ave., and see the 3-story glass globe, which gives a 3-
D perspective of the world in 1935.
(marybakereddylibrary.org/exhibits/mapparium)
5. Sit by the 600-foot long reflecting pool or go for a dip in the spray
fountain at the Christian Science Center.
6. Take a Duck Boat Tour. bostonducktours.com/

2. 7. Appreciate the architecture of Old South Church, 645 Boylston Street, designed in Gothic Revival style.
en.wikipedia.org/wiki/Old_South_Church
8. Visit the McKim Building and see Bates Hall as well as the inner courtyard at the Boston Public Library. bpl.org
9. Did you know that great areas of Boston are comprised of landfill? Boston, as a humanly made city, has more
artificial acreage than any major city in the world. Visit the Norman
B. Leventhal Map Center at the Boston Public Library.
maps.bpl.org/
10.Enjoy Trinity Church, one of the “10 buildings that changed
America.” trinitychurchboston.org/
11.Look for the Tortoise and the Hare Statue in Copley Square.
12.Stop at the Boston Public Garden, the most beautiful park in
America and study the Ether Statue in the Boston Public Garden
and don’t forget to cross the “Bridge of Size.”
13.While in the Public Garden, solve two historic questions: Why is
George Washington’s horse standing on three legs and what happened to Charles Sumner on the floor of the of
the United States Senate? friendsofthepublicgarden.org/
14. Relax in the Boston Common. It is the oldest park in the United States. In 1634, the government of Massachusetts
purchased land from a Boston settler for use as a public
livestock grazing area. Boston Common was never used
exclusively for grazing, however. It also served as a public
green. Official functions such as hangings, parades and drills
took place there, and British troops camped there. It was not
until 1830 that cattle grazing was prohibited.
en.wikipedia.org/wiki/Boston_Common
15.Enjoy the Esplanade and stop at the Hatch Shell.
esplanadeassociation.org/
16.Sail with Community Boating in the Charles River Basin.
community-boating.org/
17.There is little left of the old West End of Boston. In June 1894, Reverend Ruben Kidner of the Mission of St.
Andrew offered the basement of his church at 38 Chambers Street, rent free, to the founders of Cotting School.
The doors to Cotting School opened on October 1, 1894. To learn about Chambers and other "lost streets" of
Boston, visit the West End Museum, 150 Staniford Street, thewestendmuseum.org.
18.The Vilna Shul at 18 Phillips Street, is the Center for Jewish Life and Heritage in Boston and one of the few
buildings to survive the destruction of the West End. vilnashul.com/

3. 19.Play the Charlestown Bells on the Charles River Locks. bostonglobe.com/metro/2013/10/07/artist-paul-matisse-
community-save-charlestown-bells/eeNEQpPU9OOEuAKLHhzrUJ/story.html
20.Visit Paul Revere Park in Charlestown. bostonharborwalk.com/placestogo/location.php?nid=1&sid=3
21.Enjoy the Bunker Hill Monument. nps.gov/bost/historyculture/bhm.htm
22.Stop at the Charlestown Navy Yard.
nps.gov/bost/historyculture/cny.htm
23.Visit Old Ironsides. ussconstitutionmuseum.org/
24.Enjoy the John Harvard Mall in Charlestown.
facebook.com/TheJohnHarvardMallInitiative
25.See the Boston Bruins or Celtics at the TD Bank Garden.
26.Look for the site of the Boston Molasses Disaster.
bostonglobe.com/metro/2013/08/13/molasses-disaster-boston-
north-end-showed-lethal-power-thick-
substances/nbhChG332PTOLTAnd7L6DL/story.html
27.Stop at the mouth of where the Charles River and Boston Harbor
come together near Langone Park on Commercial Street in the
North End.
28.And while you are at Langone Park, play Bocce with the locals.
northendwaterfront.com/living/playingbocce1/
29.Enjoy a meal at Massamino’s at 207 Endicott Street one of the North End’s best
restaurants. massiminosboston.com/
30.Explore Copp’s Hill. cityofboston.gov/freedomtrail/coppshill.asp
31.Visit The Old North Church at 132 Salem Street and recite Longfellow’s poem, “The
Midnight Ride of Paul Revere.” oldnorth.com/
32.Grab a pizza at Pizzeria Regina in the North End.
pizzeriaregina.com/
33.Visit Bova’s Bakery at 132 Salem Street at 3 a.m. They are
always open.
34.Enjoy Hanover Street and eat a cannoli at Mike’s Pastry.
35.Explore the Harbor Walk in the North End and Battery,
Borroughs, Union, Lewis and Commercial Wharfs.
bostonharborwalk.com/
36.Explore Christopher Columbus Park. foccp.org/
37.Take a trip to the other side of the harbor and see East Boston.
citywatertaxi.com/
38.Visit Piers Park in East Boston.

4. 39.Try the lamb barbeque and the pizza at Santarpio’s, 111 Chelsea Street, East Boston, MA. santarpiospizza.com/
40.Enjoy Candlepin Bowling at Central Park Lanes at 10 Saratoga St., East
Boston.
41.Explore the East Boston Greenway. bostonnatural.org/gwyeb.htm
42.Find the statue of America’s great builder of Clipper Ships, Donald
McKay in East Boston.
43.Stop at Logan Airport and welcome someone to Boston.
44.Return to downtown Boston and explore the entire Rose Kennedy
Greenway. rosekennedygreenway.org/
45.The New England Holocaust Memorial is a beacon of memory and hope.
It is located at 98 Union Street. www.nehm.org/
46.Look at the plants in the Mother’s Walk Park, Fort Point Channel Parks Garden or
Rings Fountain at night.
47.Enjoy the food trucks and the summer farmers’ market in Dewey Square.
48.Look for the bamboo near the River Stream Fountain at the edge of China town.
49.Stop at the Armenian Heritage Park.
50.Grab a cup of coffee and enjoy the people in Norman Leventhal Park.
normanbleventhalpark.org/
51.Visit the observation deck of the Custom House, 3 McKinley Square, at 2pm –
Monday-Thursday for a view from what once was Boston’s tallest building.
52.Enjoy Faneuil Hall and the Faneuil Hall Marketplace. faneuilhallmarketplace.com/
53.Look for the site of the Boston Massacre. bostonmassacre.net/
54.Walk through the Granary Burying Ground, Tremont and Park Streets.
freedomtrail.org/freedom-trail/granary-burying-ground.shtml
55.Take a peek at King’s Chapel, 58 Tremont Street. kings-chapel.org/
56.Look at the paintings by Allen Rohan Crite in the Boston Athenaeum,
10½ Beacon Street. bostonathenaeum.org/
57.Visit the Massachusetts State House and ask for a tour.
sec.state.ma.us/trs/trsgen/genidx.htm
58.Visit the Robert Gould Shaw and the Massachusetts 54th
Regiment
Memorial across from the State House.
nps.gov/boaf/historyculture/shaw.htm
59.Stop at the Museum of Afro-American History on Beacon Hill at 8
Smith Court and 46 Joy Street.
60.Explore the Black Heritage Trail. afroammuseum.org/trail.htm

5. 61.Look at Louisburg Square on Beacon Hill.
62.Visit Beacon Hill’s Acorn Street, the most photographed street in Boston.
63.Enjoy some old fashion German food at Jacob Wirth (jacobwirth.com),
founded in 1868. Their motto is, “We haven’t changed for the better. We
haven’t changed for the worse. We haven’t changed, period.”
64.Explore the streets of Chinatown.
(boston.com/travel/boston/neighborhoods/chinatown/)
65.Find the paifang on Beach Street.
66.Shop at one of the many markets like Chung Wah Hong at 55 Beach Street.
67.Eat with the locals at Gourmet Dumpling House at 52 Beach Street in
Chinatown.
68.New England Medical Center, 800 Washington Street, in Chinatown is one of
Boston’s finest hospitals. In early years it was Boston Floating Hospital for Children.
Today, you won’t find the old ship. Find the “Bear” that moved the New England
Medical Center from the former FAO Swartz location in Back Bay.
69.Explore the façade of South Station, Boston’s largest train station. Although it is
called South Station, it is the northern terminus for Amtrak.
en.wikipedia.org/wiki/South_Station
70.Enjoy Bay Village, Boston’s smallest neighborhood which consists of 6 square blocks
and about 700 residents. bayvillage.net/
71.Find the location of the Coconut Grove. On November 28th 1942, a huge fire
occurred at the Coconut Grove Night Club in Boston in which 492 people perished.
The Coconut Grove was originally a speakeasy—an illegal bar
during alcohol Prohibition—and some of its doors were bricked
up or bolted shut. The main entrance to the club was only a
revolving door. There were flammable decorations throughout
the building including cloth drapery and paper palm trees. The
club had a licensed capacity of 500 people, and on the night of
the fire there were about 1000 people in the building. All of the
above contributed to the tragedy. (Source: Celebrate Boston)
cocoanutgrovefire.org/
72.Eat breakfast or lunch at Mike & Patty’s at 12 Church Street.
mikeandpattys.com/

6. 73.Enjoy Boston’s Seaport District. bostonmagazine.com/2012/07/rise-seaport-
district-boston/
74.Try a nice meal at Sportello’s at 348 Congress Street.
zagat.com/r/sportello-
boston
75.Sit along the water at the Institute of Contemporary Art. icaboston.org/
76.Are you a kayaker? There is a public access dock along Fort Point Channel
with excellent access to Boston Harbor. fortpointpier.com/
77.Return by way of Fort Point Channel, where there are walking paths that will
take you to the Broadway Bridge in South Boston.
friendsoffortpointchannel.org/
78.Enjoy the richness of South Boston.
cityofboston.gov/neighborhoods/southboston.asp
79.Enjoy the restaurants along Broadway.
80.Visit Dorchester Heights (Thomas Park in South Boston), where the Patriots drove
the British out of Boston. en.wikipedia.org/wiki/Dorchester_Heights
81.Stop at Joseph’s Italian Bakery in South Boston for a square slice of pizza. Ask for
the corner piece! josephsofsouthie.com/
82.At the end of East Broadway gaze with Admiral Farragut upon the Atlantic.
83.Stop at Sully's for what the locals call a “snap dog.” sullivanscastleisland.com/
84.Explore Fort Independence on Castle Island. Free-guided tours begin on
Memorial Day Weekend. bostonfortindependence.com/
85.Enjoys the views from the “Sugar Bowl” mapmyrun.com/us/south-boston-
ma/south-boston-sugar-bowl-route-938419
86.Take a swim at Carson Beach.
bostonharborwalk.com/placestogo/location.php?nid=6&sid=45
87.Travel to the South End and see the largest Victorian District in the United
States. south-end-boston.com/
88.Explore historic South End Squares like Union, Blackstone, Franklin and
Worcester.
89.Find the wooden house on Haven Street in the South End.
90.Hungry, grab a bite at Mike’s City Diner at 1714 Washington Street.
mikescitydiner.com/

7. 91.Find the neck of Boston. Hint: It's near Peter’s Park in the South End.
92.Why was Dover Street renamed East Berkeley Street and whatever happened to the New York Streets area of the
South End?
93.Find the site of the 1919 Boston Police Strike. Hint: It is
near JJ. Foley’s in the South End. jjfoleyscafe.com/
94.Boston is full of “urban ghosts” reminders of our past
that often go completely unnoticed. Sometimes they
are outlines of long gone buildings. Other times they
take the form of worn away advertisements. As you
explore Boston, find as many “urban ghosts” as
possible. A fine example can be found at the corner of
Union Park Street and Harrison Ave. in the South End.
95.Visit Villa Victoria and enjoy a meal at Vejigantes
Restaurant at 57 West Dedham Street in the South
End. vejigantesrestaurant.com/
96.Stop at Tremont Drug at 610 Tremont Street and enjoy a
“classic slush” at a family owned pharmacy.
97.Volunteer at Haley House (haleyhouse.org/) a soup kitchen
at 23 Dartmouth Street or Pine Street Inn (pinestreetinn.org/),
New England’s largest shelter and provider of affordable
housing at 444 Harrison Ave.
98.Experience Boston’s SOWA First Friday’s by visiting the area
South of Washington Street to experience the SOWA Artists
Guild. (facebook.com/sowafirstfridays)
99.What is a cyclorama? Once the site of the mural of the
painting of the Battle of Gettysburg, this facility at 539
Tremont Street has had multiple uses. Explore.
bcaonline.org/venues/cyclorama.html By the way, did you
know that most of the South End was built on landfill. Find Boston Groundwater
Trust wells in the sidewalks. bostongroundwater.org/
100.Enjoy the Harriet Tubman Statue at the corner of Columbus Ave and Columbus
Square.
101. What was once a dark depressed railroad bed in the South End is now a vibrant
urban park. Stroll the Southwest Corridor Park. swcpc.org/

8. 102. South End and Lower Roxbury were once a Jazz Mecca. Top African–
American artists including Duke Ellington and Cab Calloway played in places like
the Hi-Hat and The Savoy. Now only Wally’s at 427 Mass Ave remains.
wallyscafe.com/music_schedule.htm
103. Hungry, stop for a bite at Flour Café at 1595 Washington Street.
flourbakery.com/
104. In 1959, the automobile won the land battle and Chester Square was cut in
two. en.wikipedia.org/wiki/Chester_Square_(Boston)
105. Explore the Black Women’s Heritage Trail in the South End
bwht.org/south-end/ and Roxbury bwht.org/roxbury/
106. Take some time to explore Roxbury and consider a walking tour.
discoverroxbury.org/
107. Discover Dudley Square, the commercial center of Roxbury.
en.wikipedia.org/wiki/Dudley_Square
108. Enjoy a meal at the Haley House Bakery Café at 12 Dade Street, Roxbury. A
model of social enterprise, Haley House Bakery Café promotes the physical,
economic and social well being of the community. Its programs provide on-the-job
training for those seeking to become financially independent and introduce young
people to the power of cooking from scratch and making other healthy life-style
decisions. haleyhouse.org/bakery_cafe
109. Visit the First Church of Roxbury in John Eliot Square. Boston's oldest
surviving wooden meetinghouses from the Federal Period of American architecture.
en.wikipedia.org/wiki/John_Eliot_Square_District
110. Tour the Dillaway-Thomas House in the Roxbury Heritage State Park.
mass.gov/eea/agencies/dcr/massparks/region-boston/roxbury-heritage-state-
park.html
111. See Roxbury High Fort, the site that once contained earthwork fortifications
for the Continental Army during the Siege of Boston.
en.wikipedia.org/wiki/Roxbury_High_Fort
112. Visit First Mosque of Roxbury, the Islamic Society of Boston at 100 Malcolm X Blvd near Roxbury Crossing.
isbcc.org/
113. Visit the Basilica and Shrine of Our Lady of Perpetual Help, known as the Mission Church and look for the
umbrellina. en.wikipedia.org/wiki/Basilica_and_Shrine_of_Our_Lady_of_Perpetual_Help

9. 114. Appreciate the magnificent health facilities in the Longwood area like
Children’s Hospital of Boston where in 1893, Drs. Bradford and Thorndike
founded Cotting School. childrenshospital.org/
115. Explore Boston’s Emerald Necklace and give thanks to Frederick Law
Olmstead. emeraldnecklace.org/
116. Find Daniel Chester French’s statue to John Boyle O’Reilly statue at
the edge of the Back Bay Fens. French designed the Lincoln Memorial.
en.wikipedia.org/wiki/Daniel_Chester_French
117. Enjoy the sights and sounds of Kenmore Square.
kenmoresquareboston.com/
118. Visit Fenway Park, at 4 Yawkey Way and maybe you’ll be
lucky enough to see a Yankees – Red Sox game. Tours are
available and you can see Pesky’s Pole, the Ted William Seat in
right field, the Triangle in center field and the Green Monster in
left field.
119. Visit the Museum of Fine Arts, 485 Huntington Ave.
120. Let’s end our tour with a nod to one of Cotting School’s most
generous benefactors, Isabella Steward Gardner and stop at her
museum at 280 Fenway. Thanks to “Mrs. Jack’s” generosity
Cotting School’s former facility at 241 St. Botolph Street, was more
then doubled in 1926. The estate of Isabella Steward Gardner left
funds to her museum, Cotting School, Massachusetts Society for
the Prevention of Cruelty to Children, Animal Rescue League and
Massachusetts Society for the Prevention of Cruelty to Animals.
Enjoy her extraordinary museum and appreciate all that she did for
Cotting School. gardnermuseum.org/home

10. This interactive Google Map is available at https://mapsengine.google.com/map/edit?mid=zs5-hxYGLTWg.kv9-UTAWgARA