By any measure, Boston is one of the world’s great running cities. Miles of waterfront trails, an abundance of public parks and comfortable running temperatures from April to November make Boston a very approachable place to get out for a jog, or if you’re so inclined, a marathon. These flat, pedestrian friendly four-milers (about six kilometers) are a scenic way to see Boston, from Downtown to its outer neighborhoods.
The Charles River Loop: Boston, Cambridge and the Marathon home stretch
This four-mile (six-kilometer) loop will take you from Boston to Cambridge and back again while circling the picturesque Charles River. Start at the Charles River Esplanade right by the Massachusetts Avenue Bridge on the Boston side. This beautiful strip of waterfront park is incredibly popular with runners, walkers, cyclists, rollerbladers (yep, still) and even sailors – Boston’s popular Community Boating sailing school is anchored here. Head east towards the Longfellow Bridge, identifiable by its towers that resemble salt shakers, as well as the Red Line subway tracks running through its center. There are a few paths to follow in the Esplanade here, but the rule of thumb is to stay close to the river (and away from the road) for the best views and most serene route. Put your willpower to the test as you pass Night Shift Brewery’s Owl’s Nest beer garden (open from late spring to early fall). Better yet, stop by for a cool-down beer after your run. Off to your right you’ll pass the Hatch Shell, Boston’s iconic outdoor performance space that hosts the annual Boston Pops July 4th performance (as well as other concerts and free outdoor movies throughout the summer months).
Destinations Unlocked:Let our travel expert Stefano help you find your perfect Culture trip
Looking for an expert's perspective?Uncover my top 3 recommended places from each continent on the map.
1. GuatemalaAn express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.
2. BelizeA quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
3. MexicoAn exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
1. EcuadorA remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.
2. PeruAn alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
1. ItalyThe ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.
2. ScotlandEmbark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
3. PortugalA wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
1. South KoreaDiscover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.
2. ThailandFrom Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
3. Sri LankaA fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
1. MoroccoAn epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!
2. EgyptFrom Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
As you approach the historic Longfellow Bridge, look out for the stairway/ramp to the bridge, the safest way to access the pedestrian path over the bridge. Keep on the left-hand side of the bridge as you cross for spectacular views of the Charles River, the Esplanade and Boston’s skyline in the background. Once over the bridge, you’re in Cambridge, Boston’s sister city, known for its universities and its cool bars and restaurants. Once you pass the last of the bridge’s salt shakers, hang a left to get back on the river path (now on the Cambridge side across the river from the Esplanade), looping back in the direction of the Mass Ave Bridge. Along this stretch you’ll get smarter just breathing in the air as you pass MIT’s campus on your right. On your left, you’ll have an uninterrupted view of the Charles River and Boston, as well as Cambridge’s scenic marinas and sailing clubs. Once you reach the Mass Ave Bridge, hang a left and cross back over to Boston, and get ready to cue up ‘Eye of the Tiger’– you’re entering the final half-mile of this route, which also happens to be the final half-mile of the Boston Marathon.
Taking a left onto Commonwealth Avenue, you’ve now entered the home stretch of perhaps the most famous road race in the world. As you take a right onto Hereford Street, imagine the crowds of people cheering you on after 26 miles (42 kilometers) of running. Hang a left onto Boylston Street and you’ve entered the final straightaway – only three more blocks to the finish. As you zoom past Exeter Street, keep a careful eye on the middle of Boylston Street between Exeter and Dartmouth streets, in beautiful Copley Square and steps from the Copley subway stop on the Green Line – there, painted permanently in blue and gold, is the Boston Marathon Finish Line. Nice work, champ!
Boston Harbor: Castle Island to JFK Library
Start at Sullivan’s snack bar in South Boston, or ‘Southie’ as it’s affectionately known. This fast-food institution serves as the gateway to Castle Island, a charming 22-acre (nine-hectare) park jutting into Boston Harbor. Entering Castle Island park, take the trail up to your left-hand side to begin your run. Off to your left, the Conley Shipping Terminal, stacked with shipping containers and industrial machinery, may seem like an eyesore on this beautiful stretch of coastline. But from the right perspective, the checkerboard of multicolored containers and flanked by blue and white cranes has a modern art vibe, and is worth a photo. On your right-hand side you’ll see the centerpiece of the park, Fort Independence. With roots dating back to the 17th century, this former military fortress was used as a military outpost throughout America’s wars and conflicts up through World War II, and is now a museum. Unless you’re a military history buff, it’s more interesting as a scenic backdrop than a tourist site in its own right. Stay left along the ocean as you run through the park.
As you round the fort, take a quick detour out to the stilted fishing pier just off the walking path. Most days it will be dotted with fishers trying to reel in some cod for dinner. These anglers are almost always approachable and willing to let you take a look at their catch or tell you about the day’s conditions. Now on the far side of the fort, instead of looping back to where you started, head straight out on the thin spit of land called the Head Island Causeway, part of Boston’s Harborwalk. You’ll see some of the Boston Harbor Islands off to your immediate left, but after that it’s open ocean. From here on out, you’ll follow the coastline for about 2.5 miles (four kilometers), past South Boston’s beaches, which cater to a mix of local families and college grads during the summer months. Once the sandy beaches end, you’ve entered Dorchester, Boston’s largest neighborhood – more than 20% of Boston’s population lives here. The neighborhood’s main drags are worth a visit especially when hungry, as you can get just about any type of authentic cuisine here due to the neighborhood’s size and mix of long-timers and immigrant communities.
Finish your run as you approach the modern black and white blocks of the JFK Library, near the Red Line of the T.
Side note: While famous in its own right, the JFK Library is still one of Boston’s most underrated museums, likely due to its location outside of the major tourist zone. The building itself, whether it’s your style or not, offers a thoughtful counterpoint to the traditionalism of Boston’s red-brick architecture. In fact, Jackie Kennedy hand selected the then relatively unknown architect IM Pei to design the building. Inside (and you should go in, even if you’ve broken a sweat), the exhibits are varied but consistently fascinating regardless of your level of interest in Kennedy himself.
The Emerald Necklace: Fenway to Jamaica Plain
Start at the Verb Hotel, right across the street from Fenway Park.
This run takes you along the well-maintained trails of Boston’s Emerald Necklace park system. Designed by Frederick Law Olmsted, famed designer of Central Park in New York (and let’s face it, probably the only park designer most people have ever heard of), the string of parks traverses the entire city of Boston. This is a real gift for runners, as there’s minimal traffic and you have a choice of sidewalk or dirt path for much of the route.
From the Verb, head right on Ipswich Street and then left on Boylston and you’ll run smack into the The Back Bay Fens, a park that will serve as your entry point to the Emerald Necklace. From here, follow the green spaces – the Emerald Necklace snakes right through the city. The serene path twists and turns through some community garden plots on the north side of the Fens and then later past Boston’s museum district on the south side, where you’ll pass the regal Isabella Stewart Gardener Museum and Beaux Arts-inspired architecture of the Museum of Fine Arts Boston. After crossing Brookline Avenue and the Riverway, you’ll see a large sign for the Emerald Necklace, so you’ll know you’re going the right way.
In this Riverway stretch, you’ll be running parallel to the T Green Line train tracks. They’re not renowned for their speed, so you could probably beat one of these green trolleys in a foot race to Longwood Station if you’re looking for motivation. Keep in mind that one side of the park has a paved path and the other side is a dirt trail, so choose whichever option is better for your legs. The small river running in between is the dividing line between Boston (to the east) and Brookline, birthplace of some of Boston’s favorite sons, including JFK, RFK and Conan O’Brien – and adoptive home of its sports hero, Tom Brady. Onward past the intersections near the renowned Longwood Medical Area (home to some of the best hospitals in the world) is Olmsted Park. Here, you’ll pass some solitary ponds, geese and other large birds, and some shockingly wild-looking trails hidden beyond the sight of cars. Finally, the green turns to Jamaica Pond, a fairly large body of water surrounded by benches, a boathouse and more people strolling and taking in the views.
End at Jamaica Pond in Boston’s hip and leafy Jamaica Plain neighborhood, where you can eat, stroll the shops or take the Orange Line back to the center of the city.
Volcanic Iceland Epic Trip
meet our Local Insider
HOW LONG HAVE YOU BEEN A GUIDE?
WHAT DO YOU LOVE ABOUT YOUR JOB?
It's the personal contact, the personal experiences. I love meeting people from all over the world... I really like getting to know everyone and feeling like I'm traveling with a group of friends.
WHAT DESTINATION IS ON YOUR TRAVEL BUCKET-LIST?
I have so many places on my list, but I would really lobe to go to Africa. I consider myself an “adventure girl” and Africa feels like the ULTIMATE adventure!
Every CULTURE TRIP Small-group adventure is led by a Local Insider just like Hanna.
KEEN TO EXPLORE THE WORLD?
Connect with like-minded people on our premium trips curated by local insiders and with care for the world
Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.
Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.