The Top 10 Things to Do in Jamaica Plain

Jamaica Pond in Boston's Jamaica Plain
Jamaica Pond in Boston's Jamaica Plain.

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Jamaica Plain, known to Boston locals as “JP,” is one of the best neighborhoods in Boston to explore, thanks to its unique charm and a strong sense of what it means to be a tight-knit city community. Here, you’ll find everything from outdoor activities like exploring the Arnold Arboretum or Jamaica Pond, to touring the iconic Sam Adams Brewery, dining at restaurants of all kinds, listening to live music, and more.

Jamaica Plain is easily accessible through Boston’s MBTA Orange Line, though this neighborhood is much easier to park in than others throughout the city. Before heading there, be aware that the popular Doyle’s Cafe recently closed, though there are plenty of other bars and restaurants to check out instead.

Here are the 10 best things to do in Jamaica Plain.

01 of 10

Go for a Walk at the Arnold Arboretum or Attend Lilac Sunday

Arnold Arboretum

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125 Arborway, Boston, MA 02130-3500, USA
Phone +1 617-524-1718

Exploring the Arnold Arboretum of Harvard University is one of the most popular—and free —things to do in Jamaica Plain, as this park is an excellent place for spending a day outdoors when the weather is nice. It’s a National Historic Landmark that was established in 1872 by landscape architect Frederick Law Olmsted as part of Boston’s Emerald Necklace. The park has 281 acres filled with plants of all kinds, from trees and shrubs to woody vines and lilacs that are studied by Harvard students and scientists from around the world.

Lilac Sunday is held at the Arnold Arboretum each year in May and is among the best flower festivals in all of New England. This is the perfect time to capture photos of and with the Arnold Arboretum’s nearly 400 lilac plants while picnicking on the grounds and participating in a variety of tours and other family activities. The Arnold Arboretum is also one of the best places to see fall foliage in Boston.

02 of 10

Have a Beer and Tour the Sam Adams Brewery

Sam Adams Brewery

 Sam Adams Brewery via Facebook

30 Germania St, Boston, MA 02130, USA
Phone +1 617-368-5080

When it comes to beer, Boston is synonymous with Sam Adams, which was born in the city back in 1984. Today, the Sam Adams Brewery, which opened in 1988, remains one of Boston’s best breweries, despite the fast growth of craft breweries throughout and just beyond the city limits. All of the Sam Adams beers were made here except for the most well-known of them all, Boston Lager, as it was made right in founder Jim Koch’s kitchen. Aside from Boston Lager, Sam Adams makes beers to fit any preferences, including limited-edition and seasonal options, with some Bostonians waiting for spring’s launch of Summer Ale and others favoring fall’s OctoberFest.

At the Jamaica Plain brewery, Sam Adams offers three different types of tours, the first being the classic tour of their beer-making process and facility, which is free and includes a complimentary tasting glass to bring home after tasting a few beers. They also have taprooms both in Jamaica Plain and now Faneuil Hall. Grab a beer at the JP location and take it onto their outdoor patio. They don’t technically serve food at the brewery, but there is often a food truck on-site, or you can take a short walk over to Ula Café or Bella Luna to pick up food to enjoy at Sam Adams.

03 of 10

Enjoy an Ice Cream or Frozen Yogurt at the Original J.P. Licks

J.P. Licks

 Courtesy of J.P. Licks

659 Centre St, Boston, MA 02130, USA
Phone +1 617-524-6740

While most Bostonians are quite familiar with J.P. Licks because they have locations in and around the city, it’s likely new to those visiting for a weekend. The name says it all: J.P. Licks was born in Jamaica Plain, so head over to the original ice cream shop for some of their handmade ice cream and frozen yogurts. 

Open since 1981, this fun-filled ice cream shop has both your everyday flavors, along with “featured flavors” like Homemade Baileys chocolate chip cheesecake, pink grapefruit sorbet and salted caramel, the latter of which is made from dairy-free oat milk. On their website, you can look up which of their popular soft-serve frozen yogurt flavors will be at each location the following week. They also make their own coffee, which you can have shipped anywhere in the U.S. as a souvenir.

04 of 10

Sample “The Beer of Jamaica Plain” at Turtle Swamp Brewing

Turtle Swamp Brewing

Turtle Swamp Brewing via Facebook 

3377 Washington St, Boston, MA 02130, USA
Phone +1 617-522-0038

If Sam Adams isn’t your thing, or if you want a smaller-scale, local brewery experience, head to Turtle Swamp Brewing. Founders—and Jamaica Plain natives—John Lincecum and Nicholas Walther opened this brewery to create a neighborhood spot to enjoy beer made with high-quality and local ingredients. With that, they call it “the beer of Jamaica Plain,” even though the Sam Adams Brewery is right in the same neighborhood. Beers at Turtle Swamp include Pale Ales, IPAs, sours, and more. Check out their events calendar to see if there’s something special happening at the brewery while you’re in town.

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05 of 10

Start the Day with Breakfast at Exodus or the Little Dipper

Exodus Bagels

 Exodus Bagels via Facebook


Start your day with breakfast in Jamaica Plain with either a quick bite to eat at Exodus, or a sit-down meal at the Little Dipper on Centre Street.

At Exodus, you’ll find the best bagels in town, which also come as sandwiches like the Monumental (egg, cream cheese, caramelized onion jam, greens) or you can build your own.

The Little Dipper has menus for brunch, all-day and dinner, with brunch taking place on Saturdays, Sundays, and Mondays. Choose from classics like the Little Dipper itself, two eggs any style with toast and home fries, or the Phoenix, a fried buttermilk-brined chicken thigh on a brioche bun with dill-chive ranch, pickles, and hand-cut fries.

06 of 10

Go Shopping on Centre Street or Buy Vintage at 40 South Street

On Centre

On Centre via Facebook 

Centre Street is where you’ll find the majority of Jamaica Plain’s shopping and dining options. One of the street’s shopping staples is On Centre, an independently owned gift shop selling everything from cards and home decor to other trinkets, clothing, and Jamaica Plain souvenirs. Other stores include Boomerangs, a thrift shop with sales benefiting AIDS treatment and prevention, Fire Opal, featuring pottery, furniture, handmade jewelry, clothing and more, and Hatched, an eco-friendly children’s boutique.

If you’re into vintage, also head over to 40 South Street, where you’ll find pieces from the 1960s to the 1980s, with new pieces rotating in and out frequently. If you can’t make it there, they also have an Etsy shop.

07 of 10

Enjoy the Outdoors at Jamaica Pond

Jamaica Pond

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Jamaica Pond, Boston, MA 02130, USA

Jamaica Pond is a great place to get outdoors when the weather is nice, whether it’s going for a walk or run along the 1.5-mile pathway or participating in other activities on the water. You can rent kayaks, rowboats, sailboats, and more at the Jamaica Pond Boat House through Courageous Sailing, where you can also sign up for lessons. If you enjoy fishing, the pond is stocked with bass, trout, and more.

08 of 10

View and Buy Local Artwork at the Aviary Gallery

Aviary Gallery

 Aviary Gallery via Facebook

48 South St, Jamaica Plain, MA 02130-3104, USA
Phone +1 617-477-4728

Started as a place for artists in the Greater Boston area to share their latest pieces, the Aviary Gallery has become a popular Boston gallery, but it isn’t your everyday gallery at all. You won’t find a traditional exhibition space here, but rather a collection of local artwork ranging from photography and jewelry to books and other crafts. The space also serves as an artist boutique and photography lab and hosts a variety of events like workshops, film screenings, concerts, and more.

Continue to 9 of 10 below.
09 of 10

Get Lunch or Dinner at a Neighborhood Restaurant


 Chilacates via Facebook

Jamaica Plain is filled with top-rated restaurants of all kinds, both on Centre Street and throughout the neighborhood. Try one of the two Chilacates locations—one on Centre Street, one on Amory Street—for Mexican street food, Scottish pub The Haven for a burger, Tres Gatos for Spanish tapas, Bella Luna & the Milky Way for pizza or Ten Tables for an upscale, farm-to-table meal.

10 of 10

End the Night with Live Music at Bella Luna & The Milky Way or the Dogwood

Bella Luna & The Milky Way Lounge

Bella Luna & The Milky Way Lounge via Facebook 

Bella Luna & The Milky Way started out as a small pizza restaurant, but quickly became a spot to go out at night as well when they took over the iconic JP Bowl candlepin bowling alley back in 1999. At the Milky Way Lounge & Lanes, they bring in live bands and host events like karaoke, comedy shows, burlesque shows and much more. In 2008, they relocated to the Haffenreffer Brewery Complex on Amory Street but residents of JP continue to love Belly Luna & The Milky Way for its food and entertainment, along with the owners’ commitment to building and supporting the local community.

Brick oven pizza restaurant The Dogwood also has live music on Fridays and Saturdays that can be enjoyed while sitting out on their outdoor patio.

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The Top 10 Things to Do in Jamaica Plain