The Perfect Weekend Guide to Outdoor Adventure around Boston

Robbie Shade
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Fast-paced, history-laden, and brimming with energy, Boston is a common destination for adventurers in search of uncommon experiences. This New England bastion is a one-of-a-kind destination, featuring both urban and outdoor opportunities aplenty for folks to seize. Approaching 5 million inhabitants in the Greater Boston area, visitors who come to this metropolis will quickly discover what keeps full-time residents here. Vivacious and enduring, the aura encompassing Boston is one of timeless tradition mixed with adaptability and dynamism—a way of life that out-of-towner’s will quickly recognize and love.

Here's how we recommend spending a weekend in Boston, one of the oldest, most cornerstone, characterful cities in the country.

Where to Get Caffeinated

Diesel Cafe is a go-to spot for locals seeking an excellent cup of Joe
Diesel Cafe is a go-to spot for locals seeking an excellent cup of Joe Meaghan O'Malley

Visitors to Boston will find more coffeehouses than they could ever shake a stick at, but they'll quickly discover that not all are created equally. Rather than stopping by a Dunkin’ Donuts or Starbucks, take a chance with some local brews that offer outdoor happenings right outside their doors.

Take Diesel Cafe, for example. Situated just 15 minutes north of Boston proper in the city of Somerville, folks who enjoy cycling with surely love what this coffee-mecca has to offer. Bustling, yet quaint, Diesel is the go-to spot for locals who love their Joe. Rather than fight the traffic, take a ride to this killer cafe, park your bike outside, and enjoy the ambiance. Don't forget to check out the billiard tables—sipping coffee and shooting pool shouldn't be missed.

Maybe cycling isn't your jam. That’s alright—there is plenty to do right downtown and much of it within walking distance. Looking to get a fine cup of the black stuff after a walk around the Boston Common? Maybe you just finished exploring Newbury Street. What about the beautiful and historic North End, with its exquisite Italian eateries and architecture? In any of these scenarios, the Thinking Cup is a unique coffee shop that should be on your radar. With three locations around the city, there's no excuse not to pop in for a sip of Stumptown coffee and B.A.L.T—a bacon, lettuce, tomato sandwich with the addition of avocado and aioli.

Where to Hit the Trail

The view of Boston from the Blue Hills observatory tower should not be missed.
The view of Boston from the Blue Hills observatory tower should not be missed. John Dill

Hiking generally isn't the first thing people think of when they hear “Boston.” That being said, there are fantastic destinations right outside the city that will surprise even the more skeptical members of your group.

Blue Hills Reservation is a definite stopping point for folks looking to get a beautiful view of the Boston skyline, and with 125 miles of trails to choose from, hikers of all abilities are sure to find trails that are right up their alley. Families and larger groups are known to frequent the Blue Hills because of the destination’s well-marked trails, stellar vantage points, varied terrain, and close proximity to the city.

Another destination worth checking out is Harold Parker State Forest. Known for its accessibility, this state forest lays claim to over 3000-acres of land and 35 miles of trails that loop and wind around the forest, taking hikers through rock outcroppings, wetlands, high points, and 11 different ponds.

Finally, if these two destinations sound all well and good, but you're looking for adventure on the next level, consider the Metacomet/Monadnock Trail. Clocking in at 114 miles long, this trail snakes across the Pioneer Valley from Massachusetts through New Hampshire. Lakes, rivers, cliff faces, and even waterfalls dot the landscape. Paired with summit views of Mount Monadnock, Mount Tom, and Mount Holyoke, the M+M trail is the avid-hiker’s dream. And of course, quick out-and-back day hikes are always a worthy option.

Where to Go Climbing

Climbing Crow's Nest at Rumney
Climbing Crow's Nest at Rumney Robbie Shade

So many types of rock and so little time to explore them all, the Boston area plays hosts to a multitude of climbing destinations. Fields of gneiss, granite walls, puddingstone boulders, schist sport climbs—each one unique from the rest and all within reasonable distance of the city. Careful planning must be had for the visitor who is on a timeline and wishes to sample all of the area’s rock climbing.

The crown-jewel of New England sport climbing, Rumney is a super destination for beginners and experts alike. Two hours from Boston, it is a bit of a drive, but one that's well worth the time. Countless well-protected routes, easy access, and camping by a beautiful river—what else could you ask for?

If Rumney is too much of a drive, consider checking out Hammond Pond, Boston’s closest climbing destination. A 20 minute drive will have you climbing on the area’s puddingstone boulders in no time. Hammond Pond is a great option for climbers looking to get a half-day of outdoor time without the day-long commitment.

Last, but certainly not least, a visit to Lincoln Woods State Park should be on the agenda if you are looking for a great area to climb with short hiking times between boulders. About 45 minutes south of Boston in Lincoln, Rhode Island, Lincoln Woods has been the go-to destination for local climbers for over 40 years. With a large concentration of boulders that are rated on the easier end of the difficulty spectrum, this is a great place to take someone who doesn't have a ton of climbing experience, yet has a ton of enthusiasm for the sport.

Where to Paddle

An urban paddle on the Charles River
An urban paddle on the Charles River Brad Hagan

The Boston area plays host to a number of rivers and countless miles of coast that paddlers of all abilities can enjoy. That said, there are a couple of standout opportunities that should not be missed upon your visit to the area.

Paddling on the Charles River, right in the heart of Boston? Yes, its a thing—and a charmingly romantic one at that. Featuring easy put in points, as well as daily rental outfitters, getting off the street and onto the water is a breeze. Consider a summer afternoon paddle and sunset picnic on the Esplanade for a picture-perfect date night. You won’t regret it.

Looking for somewhere with a bit more adventure and spice? Beginning in southern Vermont and snaking its way through western Massachusetts, the Deerfield River offers a beautiful environment for paddling. Winding through forests and towns, under bridges, and past large boulders, the scenery takes paddlers a world away from the busy city of Boston. Add in a high probability of wildlife sightings, as well as a whitewater outfitter conveniently located right at your put in point, and you have yourself a fully-stacked paddling experience of a lifetime.

Where to Unwind

Night falls, and the City of Boston comes alive.
Night falls, and the City of Boston comes alive. Robbie Shade

Boston is notorious for its fast-paced and eccentric demeanor, so visitors looking for a place to relax, yet lack the proper knowledge, can find themselves in high-energy locales with no reprieve. Don’t worry—the following destinations allow a good balance of local vibe and chill space where weekend warriors can unwind after a long day of exploration and adventure.

After climbing at Farley Ledges, The Crooked Tap is the place to go for food and beer. Home cooked meals and a killer draft selection are the norm here. Even on its busiest nights, The Crooked Tap is a far-cry from the typically animated Boston bar-scene. Enjoy your meal with the locals and wind down from all of the day’s events.

Elsewhere, the Gulu Gulu Cafe, a cafe and restaurant in a class all on its own. Located about 40 minutes from Boston, folks from varying walks of life and all areas of the world seem to congregate into the city of Salem, especially during autumn. While here, they naturally search out the best coffee, beer, and food. And time and time again, Gulu takes the cake. Although busy on weekends, this destination is a known local haunt for folks to relax and enjoy themselves amongst others looking to do the same. And with live music nearly every night of the week and a beer list that will make your jaw drop, it's easy to do just that.

Where to Get a Good Night’s Rest

Sonya Green

Boston offers some fun alternatives to the standard hotel/ motel scene.

For a nice day trip paired with an overnight like no other, Bumpkin Island should be high on your bucket list of destinations to visit while in the Boston area. A one hour paddle through the Boston Harbor or a ferry ride via Hingham Harbor will have you on the island and enjoying the sights. A unique experience altogether, this destination is probably geared more towards the more adventurous and experienced outdoor enthusiast and will certainly provide memories for years to come.

But we get it—camping on an island definitely isn't for everyone. For those who would rather the comfort of a bed after their day’s adventures, consider Hi-Boston, Boston’s highest rated hostel. Located right in Chinatown, this overnight spot allows visitors the convenience of prime location in the heart of the city. From the Charles Playhouse to the Boston Common and countless destinations in between, Hi-Boston gives its guests the ability to explore this bustling city with the benefit of being able to take a break throughout the day before heading out for the night’s activities.

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