Boston Outdoor Activities Guide

If you don’t have a boat of your own, you can reach this 114-acre isle in Boston Harbor Islands National and State Park by ferry to take advantage of its beaches, picnic areas and walking trails. Then head out to sea under your own power during one of the island’s first-come-first-serve, ranger-led sea kayaking excursions. If you’re looking to guarantee a trip, try signing up for REI’s guided paddling tours of the islands or beginner coastal kayaking classes.

It only takes about half an hour to bike from downtown Boston to this 281-acre arboretum just south of Jamaica Pond, but you’ll feel transported thanks to its globe-spanning collection of 2,173 plant species, including 180 kinds of lilac and Japanese bonsai trees up to 275 years old. Free guided tours leave from the Hunnewell Building each weekend, or simply explore the arboretum yourself. “It’s a beautiful park for walking, running and hanging out,” says Lys Cianci, visual lead at Boston’s REI store.

Running 4.1 miles from the Back Bay neighborhood to Jamaica Plain, this park’s protected path is a popular route into the city for bike commuters during the week, and on weekends, it’s perfect for getting out, be it by bike, foot, rollerblade or whatever tickles your fancy. Just don’t expect panoramic views. The inconspicuous trail passes underneath some of the area’s major roads. But with destinations like the Arnold Arboretum, Jamaica Pond and more along the way, it’s well worth the ride.  

The calm waters of this secluded oasis are a prime spot for learning watersports. Five miles south of downtown and easily accessible via the linear Southwest Corridor Park, Jamaica Pond visitors can rent sailboats, kayaks and rowboats through the nonprofit Courageous Sailing. Or sign up for a sailing lesson by calling the organization’s boathouse a week in advance. Red and white oaks and a 1.5-mile walking path surround the pond, which sits along Boston’s historic Emerald Necklace, a 1,200-acre span of parks and waterways that snakes through Boston and Brookline.

Sure it’s downtown, it’s well-known, and it’s often crowded, but the Rose Kennedy Greenway is popular for a reason: It’s like nothing else. A product of the Big Dig, this one-of-a-kind green space replaced the aboveground highways that once snaked through the heart of Boston to give pedestrians a prime avenue for exploring the amazing restaurants, historical sites and waterfront views of neighborhoods like the North End, Seaport and Chinatown. The Greenway also hosts food trucks and artisan vendors, and in summer it’s home to two different beer and wine gardens—one from the wildly popular Trillium Brewing Company and another from City Winery, a nearby wine-centric music venue.

Many local crags can’t be reached via public transportation, but Middlesex Fells is one—and then some. Situated north of Medford about 1.5 miles away from the Malden Center MBTA stop, there are plenty of boulders and short walls to send in climbing areas like Black and White Rocks, which has more than 30 beginner and intermediate trad, top-rope and bouldering routes. In total, the Fells sprawl across more than 2,000 acres of open space, mixed-use trails, fishing holes, boat launches and even a zoo.  Need an intro to climbing first? No problem. REI has plenty of beginner to advanced climbing courses for you to sharpen your skills.

You’ll find Carson Beach, the area’s best spot for outdoor swimming and the site of the city’s only triathlon, just 2 miles south of downtown. The cove opens to Boston Harbor, and its beaches have sand volleyball courts for pick-up games and recreational league play. Pack a picnic or grab a bite at one of the food vendors that line the sand. Then after a swim, stroll the Harbor Walk 2.5 miles northeast to Castle Island, where historic Fort Independence overlooks the harbor. Or, if you’re up for it, extend your journey for as long as you’d like; the Harbor Walk stretches along 43 miles of city shoreline in total.

With 115 routes, Quincy Quarries is one of the most popular climbing areas in the metro area. It is also a great place to learn the sport, says Heather Schmidt, a pastry chef and outdoor enthusiast who’s opening an adventure-centered cafe called Landsmith just north of Boston. There’s plenty of graffitied bouldering and top-roping to be had, with routes starting at a 5.5 grade. Beginners should check out the Black and White Knight trad routes, while more experienced climbers will enjoy Under the Big Top, a 5.10 roof climb. Adjacent to the quarries lies the Blue Hills Reservation, which is full of running and hiking trails for all levels, including the 7.9-mile Skyline Trail which gains a total of 1,875 feet and offers some of the best views of Boston around.

Trillium Brewing Company, the famed Boston beer maker, is everywhere in the city. You’ll find its flagship location south of town in Canton, and it recently opened a new restaurant and taproom near its original digs in the Fort Point neighborhood. And later this summer, Trillium will open a new tap house in the Fenway neighborhood, on the lawn in front of the historic art deco 401 Park. The 1,500-square-foot space will feature an open-air patio for warm-weather sipping, and in colder months, you’ll feel like you’re in a greenhouse as you watch the snow fall from behind its floor-to-ceiling glass walls.

Spanning 300 acres of shoreline on the city’s northern border, Belle Isle is Boston’s last remaining salt marsh, a type of coastal wetland that is under threat from development and climate change. It’s also one of the area’s best bird-watching sites, home to more than 270 species. Accessible from the MBTA’s Suffolk Downs Station, the reservation’s boardwalks and viewing towers, open year-round, offer opportunities to spot wildlife rarely seen in urban areas. 

This 3-mile-long waterfront promenade offers unending views of the Charles River and the city year-round. Take in spring blooms or autumn foliage, cross-country ski its snowy riverbanks or sling a hammock for a shady, summertime nap. Accessible by walking or biking from anywhere in the city, the Esplanade is also home to beer gardens, outdoor movies, free fitness classes, group runs and, of course, kayak, sailboat and SUP rentals. Plus, its riverside trail connects with around 20 miles of paths which line both sides of the Charles River.   

Everett-based Night Shift Brewing runs two beer gardens on the banks of the Charles, both of which are kid- and dog-friendly. One sits near Harvard University in Allston and the other is on the Esplanade near the Hatch Shell, the iconic art deco outdoor concert hall where the Boston Pops play their July 4 concert every year. If you’re looking for a great summer brew, try a Rickey Weisse, a sour ale with notes of raspberry and lime that’s part of the brewery’s weisse series.

More than just a straight shot out to the suburbs, this railroad-turned-multiuse-path has become a cultural touch point and was even inducted into the Rail-Trail Hall of Fame in 2008. A 20-mile, out-and-back ride from Cambridge to Bedford takes about an hour and a half, and you’ll pass plenty of parks, green spaces and historic sites such as the Hancock-Clarke House, the intended destination of Paul Revere’s famous ride. Plenty of coffee shops and restaurants just off the path make for perfect pit stops. The bike-friendly Ride Studio Cafe in Lexington, for example, provides indoor bicycle parking, maintenance services and group rides. Need a refresher on how to ride a bike, or need to learn for the first time? REI offers biking classes to get you rolling in no time.

If you’re new to sailing, don’t worry. There are plenty of places to learn, a few of which are mentioned elsewhere in this list, but this community sailing center across the water from downtown Boston is one of the best, offering a broad range of youth, adult and adaptive sailing programs. Plus, its location on the East Boston Greenway means you can have an epic adventure that’s about as good as it gets. Fuel up for it across the street at the Downeast Cider taproom and KO Pies, which specializes in small, savory Australian hand pies.   

Water is the big draw at Beaver Brook, a 59-acre public space west of the city in Belmont. During the hot summer months, families come for the outdoor swimming area that features a spray deck with streams of arching water perfect for kids to splash. Or head north along the reservation’s paved and groomed walking paths past several ponds to find a 30-foot-tall waterfall. Before you cool off by the water, work up a sweat at the reservation’s athletic field or bring your mountain bike. The area is filled with beginner and intermediate fat-tire trails like the flowing and technical Coal Road Singletrack.