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Guide to Boston Outdoors

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Hiking, biking, kayaking, walking... Boston is a great city for exploring the great outdoors. Here are some of my favorite "fresh-air spots" in the city and the surrounding areas.

Good for
  • History Buff
  • Thrill Seeker
  • Nature Lover
  • Thrifty Traveller
  • Like a Local

9 Places

4 City Tips

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Map

9 Places

Hubway Bike Rental

Equipment Hire

Middlesex Fells Reservation

Nature & Wildlife Areas

Boston Common

Parks

Freedom Trail

Historic Walking Areas

Charles River Esplanade

Jogging Paths & Tracks, Parks

Blue Hills Reservation

Nature & Wildlife Areas

Charles River Canoe & Kayak

Kayaking & Canoeing

Boston Harbor Islands National Recreation Area

Islands, National Parks

Newbury Street

Points of Interest & Landmarks

Vincent M's City Tips

  • You can buy paper tickets for "The T" (transit system) at any machine, but ask an attendant for a Charlie Card, to which you can add credit – it ends up being cheaper.
  • Please recycle the Charlie Card when you are done with it. Baskets are available at all the stops, or you can give your card to any transit employee.
  • Boston is a small(ish) city, so don't be afraid to walk – it only takes a couple of minutes to walk between some train stops.
  • When dining out in Boston, it is customary to tip 15-20% of your restaurant bill, or $1 per drink at the bar.
  • Save
    Hubway Bike Rental
    Equipment Hire
    See more photos
    Vincent M Says:

    Boston's bike-sharing program has stations are all over the city, making it easy and affordable to explore on two wheels. While primarily a 'local' mode of transit, selling monthly and annual memberships, Hubway also offers 24- and 72-hour passes that allow you to take as many rides as you like within your given period of time. Boston is small enough that you can easily cover a large part of the city in a single day of riding. And with Hubway, you can ride to one destination, drop off your bike at a nearby station, and then pick up another one later – without the hassle of figuring out where and how to lock up your wheels in between.

    Good for
    • Thrill Seeker
    • Thrifty Traveller
    • Nature Lover
    Tips
    • Download the app to find docking stations. The app will also tell you whether or not a given station has bikes or parking spaces available.
    • Hubway Bike Rental is slightly more expensive than riding "The T", but riding a bike is a fun experience – and a better way to see the city than sitting on a train or bus.
    • By renting a bike from Hubway, you agree to wear a helmet. Select kiosks feature "Helmet Hub" rental machines. Check the website in advance for locations.
    • Be sure to bike safely in Boston. Stick to bike lanes, follow traffic signals, and be mindful of car and foot traffic.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #30 of 66 Outdoor Activities in Boston
    • Good experience. Needed customer service and it was prompt. 03/03/2018
    • Great way to see the sights! 17/10/2017
    • Hubway Bike Rental
    Phone:
    1-855-9-948-2929
    Other:
  • Save
    Middlesex Fells Reservation
    Nature & Wildlife Areas
    Vincent M Says:

    Less than 10 miles north of the city, you can access the Middlesex Fells Reservation from either Medford or Malden (both Boston suburbs). Within the reservation, you will find some easy hiking trails that lead up to a panoramic view of the city. It's a bit challenging to reach the Fells via public transportation, but the lush escape is well worth the trek. The chances of seeing other people is slim and if you do they will likely be locals.

    Good for
    • Peace and Quiet Seeker
    • Thrill Seeker
    • Thrifty Traveller
    • Hidden Gems
    • Nature Lover
    Tips
    • Keep going up, as the view from the top is a must-see.
    • Try to time it so you can see the sunset from the top – there is enough time to make it back to the bottom before dark.
    • For the West Side: Take the Orange Line to Wellington Street, and then bus #100 to Roosevelt Circle Rotary. From there, it's a short walk to the Bellevue Pond entrance.
    • For the East Side: Take the Orange Line to Oak Grove Station, and you're a short walk from the Gate 58 entrance, at the east end of the Cross Fells Trail.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #2 of 8 things to do in Malden
    • hiking fun 07/06/2018
    • Nice place for walking or hiking if you are nearby 04/03/2018
    • Middlesex Fells Reservation
    Address:
    127 E Border Rd # 159
    Malden, MA 02148
    Phone:
    +1 617-727-5380
    Hours:
    Mon - Fri
    08:45 - 17:00
    Other:
  • Save
    Boston Common
    Parks
    See more photos
    Vincent M Says:

    So you are in the city but fancy seeing some greenery, and maybe finding some peace and quiet? Historic and stunning, Boston Common is just the place for you. Established by the Puritans in 1634, the Common is the nation's original public park, and its nearly 50 acres are an inviting respite from the chaos of the city. Here you'll find plenty of green grass to set up a picnic, settle down and read, or toss around a frisbee for a while.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Thrill Seeker
    • Thrifty Traveller
    • Nature Lover
    Tips
    • If you aren't up for packing a picnic lunch, don't worry. There are plenty of restaurants all around.
    • Pay attention to the signs on the trees – you can learn a lot, and some of the ages of the trees may surprise you.
    • Boston Common is the start of the Freedom Trail, a 2.5-mile walking tour that will take you around 16 historic sites. Simply find the red line, and you're off!
    • The park is part of the Emerald Necklace, a 1,100-acre string of 9 parks linked by waterways and parkways. You can easily follow the trail to enjoy more stunning public spaces.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #39 of 413 things to do in Boston
    Certificate of Excellence 2014
    • Must visit oasis in middle of Boston 18/06/2018
    • Nice area to relax and people watch 17/06/2018
    • Boston Common
    Address:
    139 Tremont St
    Boston, MA 02111-1318
    Phone:
    +1 617-635-4505
    Other:
  • Save
    Freedom Trail
    Historic Walking Areas
    See more photos
    Vincent M Says:

    You can't come to Boston without experiencing some history. The 2.5-mile Freedom Trail will guide you through the city and into Charlestown, passing 16 major historic sites – from Paul Revere's house to Bunker Hill – along the way. The good thing about this is that Charlestown is a great, and very local, place to spend some time, making it a good introduction to the area.

    Good for
    • Must See
    • History Buff
    • Thrifty Traveller
    • Nature Lover
    Tips
    • It is perfectly acceptable to joke around with your tour guide, who will often be dressed up like they just stepped out of a time machine from the 1700s.
    • Don't expect to see the whole city, but for the half day it takes, this is a nice walk. Plan a little extra time for visiting the museums and historic sites.
    • You can explore the red-brick trail on your own, but the 90-minute tours are really worth it. The guides, who represent actual historic figures, are fun and knowledgeable.
    • Book your tour online in advance for a 10% discount.
    • The Trail offers a variety of themed tours, from Pirates & Patriots to Historic Pub Crawls. Check the "Public Tours" section of the website for descriptions and times.
    • If you're doing it on your own, download the Freedom Trail Smartphone App, which provides historic facts and amusing tidbits.
    • The "Patriot's Pass" offers discounted admission to Old South Meeting House, Paul Revere House, and Old State House. You can buy the pass online or at Old State House.
    • I would recommend this on one of your first days in the city as it could give you some ideas for what you might like to spend the rest of your time on.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #2 of 413 things to do in Boston
    Certificate of Excellence 2014
    • Awesome way to get around historic sites 18/06/2018
    • Must See! 18/06/2018
    • Freedom Trail
    Phone:
    +1 617-357-8300
    Other:
  • Save
    Charles River Esplanade
    Jogging Paths & Tracks, Parks
    See more photos
    Vincent M Says:

    Stretching roughly 3 miles from the Museum of Science to the BU Bridge, the Charles River Esplanade offers some of the best Boston views to be had from the ground. You’ll walk along a notoriously busy area of Storrow Drive, but it somehow feels serene, especially as you pass the Hatch Shell, where the Boston Pops play on the 4th of July each year. Playgrounds, marshes, and public art installations dot the area, and Cambridge sits in splendor across the water.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Thrifty Traveller
    • Like a Local
    • History Buff
    • Thrill Seeker
    • Nature Lover
    Tips
    • Sunrise and sunset are ideal times to walk/run here.
    • It's on the water, so unless you're visiting in the middle of summer, an extra layer of clothing might be useful. Check the weather.
    • Along the way, you'll spot places to rent sailboats – go for it!
    • Beware of the geese that often congregate in the area. They can be mean if you get too close.
    Plan to stay:
    1-2 hours
    From the community
    Ranked #24 of 413 things to do in Boston
    Certificate of Excellence 2014
    • Great views 15/06/2018
    • Worth cycling here 03/06/2018
    • Charles River Esplanade
    Address:
    Storrow Drive
    Boston, MA 02114
    Phone:
    +1 617-635-4505
    Other:
  • Save
    Blue Hills Reservation
    Nature & Wildlife Areas
    See more photos
    Vincent M Says:

    Stretching over 7,000 acres and encompassing a chain of 22 hills, Blue Hills Reservation is a peaceful oasis where you can take in some fresh air, get a couple hours of exercise, and enjoy some nature. At just over 600 feet, the highest hill in the chain, Great Blue Hill offers impressive views of the Boston skyline.

    Good for
    • Peace and Quiet Seeker
    • Thrill Seeker
    • Thrifty Traveller
    • Hidden Gems
    • Like a Local
    Tips
    • It's about a 30-minute drive from Boston. Avoid driving between 7-9 am and 4-6 pm, as you will hit lots of rush-hour traffic leaving the city.
    • This is a great spot to admire the New England foliage!
    • Take the Red Line to Ashmont Station or Quincy Center. From either station you can connect to buses and rail lines that will get you to your destination in the park.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #1 of 12 things to do in Milton
    • For best hiking experience in Boston 07/05/2018
    • Secret Bog! Plus great place to hike, picnic, and see nature! 02/04/2018
    • Blue Hills Reservation
    Phone:
    +1 617-698-1802
    Other:
  • Save
    Charles River Canoe & Kayak
    Kayaking & Canoeing
    See more photos
    Vincent M Says:

    While getting out on the water is great physical exercise, it's just as much a good work-out for your eyes – from your post on the Charles, you'll get a unique perspective on the city. Charles River Canoe & Kayak rents canoes, stand-up paddle boards, and a variety of kayaks (including special ones for kids). Since the company has four locations, it also offers one-way rentals, meaning you could pick up your vessel in Allston/Brighton and drop it off in Cambridge – a 5-mile trip that passes Harvard, the Hancock Building, MIT, the Hatch Shell, and more.

    Good for
    • Peace and Quiet Seeker
    • Must See
    • Like a Local
    • History Buff
    • Thrill Seeker
    • Nature Lover
    Tips
    • The weather in New England is unpredictable, so check it twice and think about bringing a rain coat anyway.
    • Pack some snacks and water for the adventure.
    • You likely wont get wet, but it's a good idea to keep electronics in a plastic bag. Just make sure they're in an accessible place, as you'll definitely want to take photos!
    • If you are staying inside Boston proper, the easiest rental locations to reach are Kendall Square or Allston/Brighton.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #10 of 43 Boat Tours & Water Sports in Boston
    • Great spot to rent a canoe, kayak or stand-up paddle board! 10/06/2018
    • Best way to enjoy the Charles 12/11/2017
    • Charles River Canoe & Kayak
    Address:
    1071 Soldiers Field Rd
    Allston
    Boston, MA 02134-1045
    Phone:
    +1 617-965-5110
    Other:
  • Save
    Boston Harbor Islands National Recreation Area
    Islands, National Parks
    See more photos
    Vincent M Says:

    The Boston Harbor Islands National Recreational Area made it onto this list in part because it's so easy to access from the city, but also because it offers such a multitude of options for spending your day(s) around the islands. From beaches and fishing to hiking and historic forts, these 12 islands offer a little something for every interest. And the ferry out provides stunning views of the harbor, to boot!

    Good for
    • Peace and Quiet Seeker
    • Thrill Seeker
    • Like a Local
    • Nature Lover
    Tips
    • Runners: Spectacle Island has a great 5k run that offers a nice change from running in the city.
    • There are 12 islands in total, so do some research to find the best one(s) to suit your interests.
    • Bird Watchers: Thompson Island is the place for you.
    • Music lovers: Check the schedule for live performances on Georges Island, if you are visiting during the summer.
    • If you feel like making an overnight adventure of your island getaway, Grape, Bumpkin, Peddocks, and Lovells Islands all offer camping.
    Plan to stay:
    More than 3 hours
    From the community
    Ranked #15 of 413 things to do in Boston
    Certificate of Excellence 2014
    • worth every bit of time 07/06/2018
    • No parking and in middle of downtown 06/06/2018
    • Boston Harbor Islands National Recreation Area
    Address:
    191W Atlantic Ave
    Boston, MA 02110-3719
    Phone:
    +1 617-223-8666
    Other:
  • Save
    Newbury Street
    Points of Interest & Landmarks
    See more photos
    Vincent M Says:

    Boston's most famous shopping street, Newbury Street is probably the busiest place on this list, but it's still fun for a day of urban outdoors. Here you'll find shopping, food, and fro-yo, plus coffee, book shops, and a healthy mix of locals and tourists interacting. It's easy to spend a couple of hours ambling and people-watching, so take your time and check out some local shops, before going on to explore some of the surrounding streets which feature great examples of Boston's famed brownstone buildings.

    Good for
    • Foodie
    • Must See
    • Trendsetter
    • Like a Local
    • History Buff
    • Shopping Fanatic
    • Nature Lover
    Tips
    • If you need a breather, take a side street and walk down Boylston Street for a while.
    • While this is one of the pricier areas of Boston, there is no charge for walking around, and a cup of coffee or an ice cream is an inexpensive pit stop.
    Plan to stay:
    2-3 hours
    From the community
    Ranked #33 of 413 things to do in Boston
    Certificate of Excellence 2014
    • Great spot for shopping 18/06/2018
    • We loved it 16/06/2018
    • Newbury Street
    Address:
    Back Bay
    Boston, MA 02105
    Other:
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