Rose Kennedy Greenway

Rose Kennedy Greenway: Our most recommended tours and activities

Boston: North End to Freedom Trail Food and History Tour

1. Boston: North End to Freedom Trail Food and History Tour

Learn about Boston's own Little Italy district of North End and its rich culinary scene. Also, learn about the significant role the city played during the American Revolution on a fascinating guided walking tour of Boston.  Make your way through to the heart of the North End, home to some of the city’s oldest buildings and renowned for its variety of food offerings. Try some fresh bread and Italian meats and cheeses at a hidden bakery. You will also indulge in some sweet local pastries. On the Freedom Trail, explore the Rose Kennedy Greenway, State Street, and the historic Custom House Tower. Then, head over to Old City Hall, which was the birthplace of public education in America. Don’t forget to get a picture of the bronzed Donkey outside the entrance Your tour will finish at the Boston Public Garden. Enjoy the rest of your day relaxing in the park and its beautiful surroundings. 

Boston: Quincy Market and North End Food Walking Tour

2. Boston: Quincy Market and North End Food Walking Tour

Eat your way through Boston’s markets and neighborhoods with a local guide. Take a private or group tour of landmarks like Faneuil Hall, Quincy Market, North End, and Paul Revere Mall. Sample Boston’s best foodie fare and hear stories of Massachusetts’ most famous city. Begin at the statue of Samuel Adams and learn about this legendary Boston resident. Your first stop is the nearby Faneuil Hall and Marketplace, a lively location close to the waterfront. Next head to Quincy Market, a bustling food hall full of colorful characters that attracts locals and visitors alike. Admire the architecture that dates back 200 years while you have some local bites. Then head into the North End neighborhood, where your guide will introduce you to the vast choice of drinks and snacks. From bread to cheeses to pizza, make sure you’re hungry because you’ll try it all. As you're munching, learn about the history of one of Boston's most iconic neighborhoods. Stroll down the tree-lined promenade of the Paul Revere Mall and snap a picture of the man himself atop his horse. Hear from your guide about the immortalized tale of Paul and his Midnight Ride. Finally, walk back to the Rose Kennedy Greenway, a picturesque park where you'll see the memorials, fountains, parks, and art exhibits that highlight Boston’s culture. Your tour ends here but your guide will gladly offer suggestions and directions on how to continue your food adventure.

Boston: City History and Highlights Audio App Walking Tour

3. Boston: City History and Highlights Audio App Walking Tour

Enjoy an ode to one of America’s historical cities on this self-guided walking tour app. Travel from Copp’s Hill Burying Ground to the George Washington Statue in the Boston Public Garden. See landmark buildings and monuments and uncover the story of the founding of the country with the audio guide. Begins in one of Boston’s oldest neighborhoods, the North End. Listen to tidbits from the Colonial and Revolutionary history of the area and travel as far back as 1692 with a visit to the grave of Cotton Mather, the minister at the hysterical heart of the Salem Witch Trials.  Journey to the Old North Church and to unlock the pre-Revolution years, when Paul Revere organized the midnight riders so they could alert the Minutemen of the arrival of the British. Breathe in the aromas of Little Italy’s restaurants and bakeries to get to the Paul Revere House. Take a stroll along the Rose Kennedy Greenway while you hear about Boston’s ”Big Dig.” Shop around the Quincy Market or catch some of the area’s regular street performers while finding out about Faneuil Hall and one of America’s fiercest proponents of liberty, Samuel Adams.  Stop by the Old State House to hear how future president John Adams magnanimously defended perpetrators of the Boston Massacre. Learn about the two choices that Irish families faced in the 1800s while passing by the Boston Irish Famine Memorial. Explore the Granary Burying Ground to see where John Adams, John Hancock, and Paul Revere are laid to rest. Soak up local stories as you hear about who sent the signal from the Old North Church steeple to Paul Revere and what Revere did after the revolution.  Engage with the past as you find out how 2 million gallons of molasses congealed in the North End in 1919. Uncover the answer to factoids like if Samuel Adams really brewed beer and what led to the creation of America’s first public park, the Boston Common.

Amazing Scavenger Hunt Adventure: Boston Harbor

4. Amazing Scavenger Hunt Adventure: Boston Harbor

Looking for a way to turn Boston Harbor area into a giant game board?  Come experience an interactive scavenger hunt that combines the fun of the "Amazing Race" with a three-hour sightseeing tour of the Harbor area. Guided from any smart phone, make your way among well-known and overlooked gems of the city, solving clues and completing challenges while learning local history. Your Boston Harbor amazing scavenger hunt adventure will begin at a serene labyrinth on the Rose Fitzgerald Kennedy Greenway and take you to historic wharves and parks with outdoor art. You'll be introduced to a small herd of seals, and view scenic harbor vistas. The game route will have you strolling down the Greenway and exploring historic harbor sites including the location of the Boston Tea Party, as the game shows you some of the best sights and hidden gems of the city. Using a smartphone as “the guide” allows participants to start when they want and determine their own pace of play. Stop for lunch along the wharf or take a stroll on one of the shaded trails of the park… why not, it’s your schedule! Offered at a fixed price for a group vs. per person pricing, this city tour/game offers a great value to those on a budget.

Boston History and Highlights: A Self-Guided Audio Tour

5. Boston History and Highlights: A Self-Guided Audio Tour

Wander along Boston's Freedom Trail with this audio guide. Walk from Copp’s Hill Burying Ground to the George Washington Statue in the Boston Public Garden and unlock the story behind the nation’s beginnings as you listen to the voice of Gregg Squeglia, a local history fanatic. Start your walk in one of Boston’s oldest neighborhoods, the North End, and learn about the Colonial and Revolutionary history of the area. Travel as far back as 1692 with a visit to the grave of Cotton Mather, the minister at the heart of the Salem Witch Trials. Next, journey to the Old North Church and the pre-Revolution years, when Paul Revere organized the midnight riders so they could alert the Minutemen that the British were coming. Waft past the aromas of Little Italy’s restaurants and bakeries to get to the Paul Revere House, before enjoying a stroll along the Rose Kennedy Greenway while you learn about Boston’s ”Big Dig.” Afterward, take a moment to shop around Quincy Market or catch some of the area’s regular street performers as you learn about Faneuil Hall and one of America’s fiercest proponents of liberty, Samuel Adams. Stop by the Old State House to hear how president John Adams magnanimously defended perpetrators of the Boston Massacre. Learn about the two choices that Irish families faced in the 1800s as you pass by the Boston Irish Famine Memorial en route to visit Adams’ grave in the Granary Burying Ground. Feel free to start, pause, or restart at any time and complete your visit at your own pace. If your travel plans change, you can use the audio guide on any date of your choice  or use the virtual in-app option for an at-home experience.

Boston: Private Seafood Tour with Local Guide and Tastings

6. Boston: Private Seafood Tour with Local Guide and Tastings

Embark on a culinary journey on a private seafood walking tour in Boston with a local guide. Walk along the Boston Harbor Waterfront and visit some of the city’s most iconic neighborhoods while sampling a meal’s worth of local foods, from flavorful clam chowder to fresh lobster rolls. After meeting your private guide for the day, head across the Rose Kennedy Greenway to two of Boston’s beloved historic landmarks: Quincy Market and Faneuil Hall. Then, visit the city’s oldest restaurant. As you walk your way through Boston, hear some only-in-Boston stories and sample classic regional dishes and responsible, locally sourced favorites as you discover why Beantown continues to be the heart of New England’s seafood scene.

Other Sightseeing Options in Rose Kennedy Greenway

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What people are saying about Rose Kennedy Greenway

Overall rating

4.8 / 5

based on 94 reviews

This is a must see guided tour of food and history in the heart of Boston. Luci B was simply amazing. The experience gave me the confidence now to explore the city on my own in the future. I do not feel as lost today exploring the city as I did when I first moved here. Thank you Luci you really are amazing.

Our guide, Tyler, was extremely knowledgeable about the history and was a great tour guide. The food was wonderful and the tour was doable even for older folks.

I did the 5 hour...3 hour history snd food, the kast 2 hours just history, I highly recommend this tour, for any age, nice slow pace, not rushed.

Detailed and easy to follow guide to Boston. Best thing is that you can pause and restart as you wish, no need to do the whole tour in one go

Fun and enjoyable walk through Boston. Easy walking pace with frequent stops see sites and eat food. Great history tour.