3 Days in Boston This Fall

October 4, 2021

Put your walking shoes on and amble down cobblestone streets dotted with American history and lined with vibrant hues of red, orange, and yellow in Boston, Massachusetts. 

Arguably the best time of the year to visit Boston, all your family memories will be enshrined with a striking backdrop of colors.

Whether enjoying the beautiful outdoors or taking in some of the spookiest gravestones and ghost stories, Boston is a must-see on everyone's fall bucket list.

Serene or Spooky?

Need some time to relax in nature and step away from the computer? Or are you craving a heart-throbbing spooky weekend?

Whether you want a Leisurely Weekend Getaway, Moderately-Paced Itinerary, or an Action-Packed Adventure, we've got your three-day Boston fall trip covered!

Leisurely Getaway Weekend

Where to Stay: Fairmont Copley Plaza

Fairmont Copley Plaza, a beautiful 1912 hotel situated between the historic Boston Library, Trinity Church, the Back Bay shopping area, and the Boston public gardens.

Day One

Where to go: Old Town Trolley Tour

Check off many Boston sights from your bucket list without the hassle of dragging little kids around a busy city with Old Town Trolley Tour tickets.  Take in the beauty of Boston in fall and give your little ones a chance to gaze and revel in a new city’s curiosities at their own pace.

Related Post: Boston Historical Sites: 21 Must-See Stops for History Buffs

Bask in the wealth of knowledge your tour guides will shower you with while on the road, but don’t forget to hop off for a closer look at these sights (stroller assistance provided):

  • Faneuil Hall Marketplace: What once used to be a meeting place to hear speeches during the Revolutionary War, this hall is now full of food for hungry families with an appreciation for history. 
  • The Freedom Trail: Walk through Paul Revere’s home, then enjoy creamy gelato and/or coffee in an authentic Italian café.
  • USS Constitution: Launched in Boston in 1797, the oldest commissioned warship still afloat. Fought the British in the War of 1812.
  • Old State House and Boston Massacre Site: See where British soldiers shot five colonists on March 5, 1770.
  • Boston Tea Party Ships & Museum (Discounted Admission): A fun and funny floating museum with interactive multimedia exhibits and live reenactments.
  • Old North Church: On April 18, 1775, two lanterns hung from the steeple of this church signaled to Paul Revere to begin his midnight ride as the British approached by sea.

boston commons area with downtown skyline in the background in Boston, Massachusetts, USA

Day Two

Where to Go in the Morning: Boston Common

Visit the Boston Common and hop in a swan boat and take a peaceful 15-minute paddleboat cruise around the Boston Garden lagoon, play a quick game of tag, have a picnic under the colorful trees, read the 1941 children’s book “Make Way for Ducklings” by Robert McCloskey and take a picture with the duck sculptures that were made in its honor. Or simply take a walk and snap some family photos in this beautiful park rich with history, including these sites:

  • The Great Elm
  • Brewer Fountain
  • John Paul II Placard
  • Central Burying Ground
  • Soldiers and Sailors Monument
  • Boston Foundation Monument

Where to Eat Lunch: The Paramount

Head north on Charles Street out of the park and get some lunch at The Paramount, a perfect eatery for kids with patio seating.

Related Post: When is the Best Time to Visit Boston?

Where to Go in the Afternoon: Charles River Esplanade

After lunch, stroll/skate/kayak/walk down the Charles River Esplanade. Stop at the playground and let the kids play while you enjoy the views. Turn left on Gloucester Street to head down to explore the shops at Back Bay.

Where to Shop: The Fairy Shop

While exploring the shops at Back Bay, make sure to stop at The Fairy Shop, a whimsical little shop currently featuring a Harry Potter theme designed by its owner.

fish in coral reef aquarium at the new england aquarium in boston

Day Three

Where to Go: New England Aquarium

After a couple of days of navigating your family around a big city, give yourselves a break and head to the New England Aquarium.

Step inside a giant ocean tank, revel at intelligent Pacific octopi, green sea turtles, and northern fur seals. You can also give your legs some rest and enjoy an IMAX or hop on a whale watching tour!

Learn More About: Boston's Top Attractions

Where to Eat: La Famiglia Giorgio’s Restaurant

Enjoy family-style Italian dining at La Famiglia Giorgio's Restaurant in this historic building which is just a 10-minute walk from the aquarium.

ground outdoor view or old town trolley tour in front of downtown buildings in Boston, Massachusetts, USA

Moderately-Paced Itinerary

Day One

Where to Stay: The College Club of Boston

The College Club of Boston is a beautiful, historic B&B in a brownstone with elegant, homey rooms.

What to Do: Old Town Trolley Tour

Check off many Boston sights from your list without the hassle of dragging kids around a busy city on the Old Town Trolley Tour.  Take in the beauty of Boston in fall and give the kids a chance to gaze and revel in a new city’s curiosities at their own pace.

Bask in the wealth of knowledge your tour guides will shower you with while on the road, but don’t forget to hop off for a closer look at these sights:

  • Faneuil Hall Marketplace: What once used to be a meeting place to hear speeches during the Revolutionary War, this hall is now full of food for hungry families with an appreciation for history. 
  • Freedom Trail: Walk through Paul Revere’s home, then enjoy creamy gelato and/or coffee in an authentic Italian café.
  • USS Constitution: Launched in Boston in 1797, the oldest commissioned warship still afloat. Fought the British in the War of 1812.
  • Old State House and Boston Massacre Site: See the spot where 5 colonists were shot by British soldiers on March 5, 1770.
  • Boston Tea Party Ships & Museum (Discounted Admission): A fun and funny floating museum with interactive multimedia exhibits and live reenactments.
  • Old North Church: On April 18, 1775, two lanterns hung from the steeple of this church signaled Paul Revere to begin his midnight ride as the British approached by sea.

Related Post: 21 Totally Free Things to Do in Boston

Day Two

Where to Go: Codzilla Thrill Boat Ride

Morning Adventure: Enough walking—see Boston from the water at double time! Embark on the Codzilla Thrill Boat Ride and welcome Autumn in Boston with the wind in your hair, ocean spray in your face, and epic music in your ears!

Where to Warm Up: Caffe Vittoria

Head past Quincy Market and up to Little Italy. Order a milky cappuccino, a warm sugary dessert, and admire the vintage décor at Caffe Vittoria.

Related Post: Current Events and Festivals in Boston, Massachusetts

Where to Shop: Commonwealth Avenue Mall

Head to the Back Bay area to stroll down the Commonwealth Avenue Mall and explore the shops. Make sure to stop in at The Fairy Shop if you’re a fan of the whimsical.

Day Three

Where to Go: New England Aquarium

After a couple of days of navigating your family around the city, give yourself a break and head to the New England Aquarium.

Go inside a giant ocean tank, see intelligent Pacific octopi, green sea turtles, and northern fur seals. You can also give your legs some rest and enjoy an IMAX or hop on a whale watching tour.

Where to Eat: La Famiglia Giorgio’s Restaurant

Enjoy family-style Italian dining at La Famiglia Giorgio’s Restaurant in this historic building which is just a 10-minute walk from the aquarium.

Evening Adrenaline: Boston Ghosts and Gravestones Tour

After dinner, join this Boston Ghosts and Gravestones Tours trolley tour to hear about the darker side of Boston by night.

Visit the city’s oldest graveyards and a haunted hotel while listening to your guide recount historic horror stories. A perfect way to end your trip if you’re in town around Halloween time!

Action-Packed Adventure

Day One

Where to Stay: YOTEL Boston

YOTEL Boston is a creatively modern hotel with SmartBeds, a 24-hour gym, and a rooftop with views.

Where to Eat Breakfast: Café Bonjour

Start your Boston weekend with an Instagram-worthy breakfast and take a coffee to go at Café Bonjour.

Related Post: What are the Most Unique Things to Do in Boston?

Where to Go: Boston Freedom Trail Walk

After breakfast, it's time to cross the street to begin the Boston Freedom Trail Walk from its starting point at the Boston Common.

Follow the 2.5 mile brick path to explore the sites where momentous events shaped the USA as we know it:

  • Boston Common: Park where colonial militias trained, public hangings took place, and British troops camped on the first day of the American Revolution. Stroll through the park, then go take beautiful photos in a swan boat at the Boston Garden.
  • Massachusetts State House: Paul Revere and Samuel Adams laid the cornerstone of this government building on July 4, 1795.
  • Park Street Church: Among other firsts, William Lloyd Garrison’s first speech against slavery, the first rendition of “My Country Tis of Thee,” and America’s first humanitarian society (the Animal Rescue League) all have roots in this church.
  • Granary Burying Ground: Dating back to 1660, Samuel Adams, Paul Revere, and the Boston Massacre victims are all buried here.
  • King's Chapel: The English king ordered the construction of this Anglican church on part of a Puritan graveyard, much to Puritan distress.
  • King's Chapel Burying Ground: The Puritan graveyard mentioned above and Boston’s oldest graveyard, many of the first English settlers are buried here.
  • Benjamin Franklin Statue: Built in 1856, this is the first public statue of a person erected in Boston. Did you know? Benjamin Franklin was the only person to sign all four of the most important documents that define U.S. democracy: The Declaration of Independence, The Treaty of Alliance with France, The Treaty of Peace with Great Britain, and The Constitution of the United States.
  • Old Corner Bookstore: Built in 1718, it once housed the company that published the works of Ralph Waldo Emerson, Henry David Thoreau, and Nathaniel Hawthorne and one of Boston's oldest brick buildings, the Old Corner Bookstore has always been a commercial space.
  • Old South Meeting House: The place where the Boston Tea Party was decided.
  • Old State House: On July 18, 1776, colonists heard the Declaration of Independence read aloud loud here for the first time in MA.
  • Boston Massacre Memorial: See the spot where five colonists were shot by British soldiers on March 5, 1770.
  • Faneuil Hall: What once used to be a meeting place to hear speeches during the Revolutionary War, this hall is now full of food for hungry families with an appreciation for history. 
  • Old North Church: On April 18, 1775, two lanterns hung from the steeple of this church signaled to Paul Revere to begin his midnight ride as the British approached by sea.
  • Paul Revere's House: The only 17th-century wood house still standing in its original Boston site.
  • Copp's Hill Burying Ground: The 2nd oldest graveyard in Boston. Colonial generals watched the burning of Charlestown and the Battle of Bunker Hill from here.
  • Bunker Hill Monument: This monument commemorates the first and deadliest battle of the Revolutionary War. 
  • USS Constitution: Launched in Boston in 1797, the oldest commissioned warship still afloat. Fought the British in the War of 1812.

Where to Eat Dinner: Pier 6

If you made it all the way to the USS Constitution Museum, reward yourself with dinner on a deck overlooking the ocean at Pier 6.

Related Post: 13 of the Top Things to Do in Boston at Night

Pier 6 is one of Boston's absolute best waterfront dining destinations, which also comes with a rooftop bar offering one of the best views in the city. Just 5 more minutes walking!

Day Two

Where to Go: Codzilla Thrill Boat Ride

Enough walking—see Boston from the water at double time! Embark on the Codzilla Thrill Boat Ride and welcome fall in Boston with the wind in your hair, ocean spray in your face, and epic music in your ears!

Where to Warm-Up: Caffe Vittoria

Stroll past Quincy Market and up to Little Italy. Order a milky cappuccino, a warm sugary dessert, and admire the vintage décor at Caffe Vittoria.

Where to Shop: Commonwealth Avenue Mall

Head to the Back Bay area to stroll down the Commonwealth Avenue Mall and explore the shops. Make sure to stop in at The Fairy Shop if you’re a fan of the whimsical.

Where to Eat Dinner: The Bukowski Tavern

The Bukowski Tavern is a hip and friendly Boston dive bar located a block away from the Fairy Shop. Cash only, peanut butter burgers, extensive beer selection.

Day Three

Where to Go: New England Aquarium

After a couple of days of navigating your family around the city, give yourself a break and head to the New England Aquarium.

Go inside a giant ocean tank, see intelligent Pacific octopi, green sea turtles, and northern fur seals. You can also give your legs some rest and enjoy an IMAX or hop on a whale watching tour.

Where to Eat: La Famiglia Giorgio’s Restaurant

Enjoy family-style Italian dining at La Famiglia Giorgio’s Restaurant in this historic building which is just a 10-minute walk from the aquarium.

Evening Adrenaline: Boston Ghosts and Gravestones Tour

After dinner, join this Boston Ghosts and Gravestones Tours trolley tour to hear about the darker side of Boston by night.

Visit the city’s oldest graveyards and a haunted hotel while listening to your guide recount historic horror stories. A perfect way to end your trip if you’re in town around Halloween time!

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