Boston/Jamaica Plain-Mission Hill

Historically, both neighborhoods were simple farming communities within Roxbury. They became part of West Roxbury during the mid-19th century for a time, before finally being annexed by Boston in 1874. Around this time a small river, or stony brook, flowed along what is today the Southwest Corridor. Taking advantage of the available hydropower, several industries sprang up along the route, most notably breweries. Residents have used Centre St and Huntington Ave for almost 200 years to commute between these factories and downtown Boston.
Possessing a wealth of green space and many transit options, Jamaica Plain is very desirable among Bostonians. The old brewery buildings have been remodeled and updated, while ever fancier shops and restaurants continue to open for business. But JP draws its real strength from the diversity of its residents. A strong character of social awareness and tolerance has mitigated gentrifications worst effects. You can still find traditional bodegas mixed in with the upscale brunch spots.
Mission Hill came into its own around 1870, after the construction of the eponymous Mission Hill Basilica. Built and paid for by the mostly German congregation, the basilica is striking and can be seen in many views of Boston. The neighborhood has changed drastically over the years. Surrounded by hospitals and universities, it plays host to a frequently rotating cast of young people. And the area affords some great views of the city from its high points.

Neighborhoods

These neighborhoods are listed from north to south. You'll find these larger nodes of activity to be separated by stretches of quieter, more residential areas. Think of the area like a wide slice of residential buildings sandwiched between giant parks on either side.

• Brigham Circle: This is Mission Hill's commercial heart. Most of the neighborhood's shops and restaurants can be found in this area. Named after the nearby Brigham and Women's Hospital, this is a transitional area of the city. Head north or "inbound" to enter the Longwood Medical neighborhood in Fenway/Kenmore. Head south-east on Tremont to continue along Mission Hill, passing the Basilica and eventually entering Roxbury. If you're feeling bold, head up Calumet Street and try to bluff your way into a house party. Your youth and a little red cup camouflage is all you'll need.
• Hyde Square: One of Jamaica Plain's commercial districts. Consisting of a tiny rotary and a bunch of fantastic restaurants and bars nearby. Later, head east down Centre Street towards Jackson Square to experience JP's "Latin Quarter". During the 70s and 80s JP was a largely hispanic area, and this section of town still reflects that today.
• The Monument: JP's biggest and busiest commercial zone. Heading north from the monument along Center Street affords the opportunity for great people watching and window shopping. If the weather's cooperating, head west to Jamaica Pond, or south-west to witness the amazing Arnold Arboretum. South will take you to Forest Hills and into Roslindale, and east will take you to Franklin Park in Roxbury.

By public transit

Taking the Orange Line and walking is the premiere way to access these neighborhoods. Roxbury Crossing serves Mission Hill, while Jackson Square, Stony Brook, and Green serve Jamaica Plain. Green is quite popular, allowing easy access to the main shopping district in one direction, and Franklin Park in the other. Use Forest Hills when visiting the Arboretum, the entrance is just across the street.
The "E" branch of the Green Line trolley is another great way into Mission Hill. Brigham Circle is the last stop along its dedicated right of way, while Fenwood Road, Mission Park, and Back of the Hill are all street level stops. Watch your step! All trolleys turn around at Heath St, the terminus of the E branch.
If you'd like to walk a little less, but wait a little more, use the #39 bus. Starting in Copley Square in the Back Bay, these big buses run constantly down Huntington Ave following the path of the E trolley. Continuing beyond Heath St and down Centre, they pass in front of every shop and restaurant in JP. Fighting traffic, they eventually make it to Forest Hills station. From Copley to Heath Street, it is arguable faster than the E branch (and a little cheaper), but they come less frequently.

By bicycle

The Southwest Corridor Park, which begins at Back Bay Station, stretches all the way to Forest Hills. It's one of the best bike paths in the city. It's also great for novice cyclists, as the path is completely separated from cars and street traffic at all times. The park runs above and alongside the Orange Line, so consider biking roughly equivalent to taking the T. There are places to lock your bike at all stations, and throughout the neighborhoods. Many locals use bikes here, so you'll never be far from a bike shop if you encounter mechanical issues.

By car

Like most other areas of Boston, driving in these neighborhoods is not a great idea. Only consider driving if you're visiting the Arboretum or Franklin Park, and strongly consider the T even then. Mission Hill borders one of the most congested areas in the city, and traffic is often snarled here at all hours. In Jamaica Plain, the main thoroughfare is called the "Jamaicaway", or Jway. This section borders the Emerald Necklace and can be particularly challenging for out of town drivers. Prepare for high speeds, narrow winding roads, and a series of busy rotaries along this four-lane undivided boulevard.

• Arnold Arboretum

  phone: +1 617 524-1718
  address: 125 Arborway
  Almost 15,000 different species of plant live in this gigantic park, covering 281 acres! Swing by the office for the particulars if you're interested, or just start exploring. Don't miss the bonsai collection, some are over 250 years old. If you want to have a picnic in this gorgeous place, make sure to do it on "Lilac Sunday", the only day picnics are allowed. It doesn't look it, but this is actually an active research facility, staffed by 20-30 people year round. Harvard University founded the Arboretum in 1872 by combining two large country estates after their owners passed. It's still owned by Harvard today. The land was deeded to the City of Boston in 1882, and leased back to the university for a thousand years. How's that for long term planning?

• Jamaica Pond

  phone: +1 617 522-5061
  address: 507 Jamaicaway
  The jewel of Jamaica Plain, Jamaica Pond is the largest body of fresh water in Boston. Surrounded by 1.5 miles of footpath, and connected to a series of other parks and ponds known collectively as "the Emerald Necklace." It's an extremely popular destination for walking, jogging, fishing, rowing, and sailing. Investigate the boathouse, where boats are available for rent during the Spring and Summer months. Due to the incident in 1929, ice skating is no longer permitted on the pond.

• Loring-Greenough House

  phone: +1 617 524-3158
  address: 12 South St
  This mid-Georgian mansion was built in 1760 as a country residence and farmstead for a wealthy British naval officer. Well preserved, this large colonial structure rests on property that includes sweeping lawns, historic flower beds, handsome trees. Call ahead to take a tour of the house and view the large collection of historical artifacts. Or just swing by in the warmer months, when the grounds are often host to festivals, markets, and other special events.

• The Mission Church

  phone: +1 617 445-2600
  address: 1545 Tremont Street
  The Mission Church broke ground in 1874 and was constructed in the Romanesque style. Built chiefly from Roxbury puddingstone quarried just across the street, in what is known today as Puddingstone Park. The stained glass windows were made by Franz Mayer and Co. from Munich, Germany. After the church opened, an icon of Our Lady of Perpetual Help was moved here. Members of the Mission began to report many cures and healed ailments. As reputed cures continued, crutches, braces, and other devices were left as votives at the shrine. The church was elevated to basilica status in 1954 when Pope Pius XII paid a visit. Senator Edward Kennedy's funeral took place here in 2009. All living presidents were in attendance, along with most of the leadership from Congress.

• Samuel Adams Brewery

  phone: +1 617 368-5080
  address: 30 Germania St
  All ages welcome for one hour tours (21+ for the tasting portion) departing every 40 minutes. No reservations, first come first serve. There is also a "Morning Mash-In" tour at 9:40AM, if brushing your teeth gets you in the mood to drink. There is of course a shop featuring exclusive t-shirts, hats and hoodies, as well as one-of-a kind beers brewed only at this location. Proust!

• Kelly Outdoor Rink

  phone: +1 617 727-7000
  address: 1 Marbury Terrace
  Outdoor ice skating rink.

• Footlight Club

  phone: +1 617 524-3200
  address: 7A Eliot St
  America's oldest community theatre features a new program every other month or so.

• Bikes Not Bombs

  address: 284 Amory St.
  Shop for a new bike, or pick up some spare parts for your current one. You could even volunteer at this charitable organization that helps get bikes to both local youths and people in developing nations.

• Salmagundi

  phone: +1 617 522-5047
  address: 765 Centre St
  Boston's best hat store. Also stocks a lovely assortment of accessories, some of which are locally made. Very friendly and helpful staff make this a fun destination in its own right.

• Boomerangs

  phone: +1 617 524-5120
  address: 716 Centre St
  Great thrift and vintage store. All proceeds go to support the Aids Action Committee, New England’s first and largest AIDS service organization. Always a good selection of clothing and furniture.

• Papercuts J.P.

  phone: +1 617 522-3404
  address: 5 Green St
  Independent, locally owned bookstore. Has special events and a podcast.

• The Video Underground

  phone: +1 617 522-4949
  address: 3203 Washington St
  The last remaining video rental store in America? Specializing in independent, cult and foreign films. The also offer all kinds of tea, coffee, smoothies, candy and snacks.

• Fire Opal

  phone: +1 617 524-0262
  address: 683 Centre Street
  Clothing, home decor, jewelry and more. One other location in Brookline.

• Caramelo Clothing Company

  phone: +1 617 942-8127
  address: 606 Centre St

• 40 South St

  phone: +1 617 522-5066
  address: 40 South St

Dining here tends to be either on the low or high end, there isn't as much selection in between. The lower cost options tend to be along the stretch of Centre from Hyde to Egleston where the long time blue collar residents live. The pricier options are popping up everywhere, with some clustering near the Monument where many wealthy new residents have landed.

Budget

• Mike's Donuts

  phone: +1 617 427-6828
  address: 1524 Tremont St
  Local donut shop where the old guys still go to get their coffee and catch up. Old school institution.

• City Feed and Supply

  phone: +1 617 524-1700
  address: 672 Centre St
  Pretty place sit with sandwiches and espresso/coffee, also to pick up (expensive but convenient) local produce and groceries.

• Pikalo

  phone: +1 617 522-1210
  address: 378 Centre St
  Dominican restaurant specializing in empanadas.

• JP Licks

  phone: +1 617 524-6740
  address: 659 Centre Street
  Flagship location for local chain that serves homemade ice cream and coffee roasted in-house. Features several different blends of fair trade coffee. In 2006, JP Licks was named the Best Coffee Shop in Jamaica Plain by Boston Magazine. Free Wifi connections available.

• Chilacates

  phone: +1 617 522-6000
  address: 224 Amory St

• Sorellas

  phone: +1 617 524-2016
  address: 386 Centre St
  A very popular spot for breakfast and brunch. Known for their dozens upon dozens of omelettes. The menu is up on the wall like Memento in this place.

• El Oriental De Cuba

  phone: +1 617 524-6464
  address: 416 Centre St
  Delightfully authentic little Cuban restaurant. A hundred framed pictures of Havana line the walls.

Mid-range

• Penguin Pizza

  phone: +1 617 277-9200
  address: 735 Huntington Ave
  Lots of good beers and thin pizzas at this friendly spot frequently on "best of" lists. The mugs on the ceiling belong to patrons who "drink around the world", imbibing a beer from every country.

• Canary Square

  phone: +1 617 524-2500
  address: 435 S. Huntington Ave
  Upscale pub food with an effort to source ingredients locally. Excellent cocktail list, but the food is overrated. Gets very crowded at peak times on weekends but the atmosphere is lively and pleasant.

• JP Seafood Cafe

  phone: +1 617 983-5177
  address: 730 Centre St
  Seafood place specializing in sushi. Also serving a variety of Japanese and Korean specialities, like bibimbop, teriyaki, and stir fries.

• Bella Luna & The Milky Way

  phone: +1 617 524-6060
  address: 284 Amory St

• Centre Street Cafe

  phone: +1 617 524-9217
  address: 669A Centre St

Splurge

• The Haven

  phone: +1 617 524-2836
  address: 2 Perkins St

• The Frogmore

  phone: +1 857 203-9462
  address: 365 Centre St
  A Southern restaurant serving "low country" food found along the coastline of the Carolinas. Order the "low country boil" to have your tablecloth replaced with newspaper and filled with andouille, shellfish, and potatoes.

• Vee Vee

  phone: +1 617 522-0145
  address: 763 Centre St

• Tres Gatos

  address: 470 Centre St
  One time book and record store turned Spanish tapas restaurant & wine bar. Vestiges of its previous life are still for sale, but the food is really the star today.

• Ten Tables

  phone: +1 617 524-8810
  address: 597 Centre St
  French/American cuisine with an emphasis on local organic ingredients. Vegetarian-friendly. The tasting menus are a little spendy, but they are an amazing value considering the quality of the fare.

• Doyle's Cafe

  phone: +1 617 524-2345
  address: 3484 Washington St
  A neighborhood landmark since 1882, and where every politician seems to smile over a pint come campaign time. Doyle's attracts an unusually diverse and friendly clientele, from tourists to neighborhood regulars. Photographs and newspaper clippings on the walls provide a fun glimpse into Boston's political history. An authentic Boston Irish pub, Doyle's features an extensive selection of aged scotches and other whiskeys. It's also known to be a backdrop for Hollywood films from time to time.

• The Galway House

  phone: +1 617 524-9677
  address: 710 Centre St

• The Jeanie Johnston Pub

  phone: +1 617 983-9432
  address: 144 South St

• Brendan Behan Pub

  phone: +1 617 522-5386
  address: 378 Centre St

• Midway Cafe

  phone: +1 617 524-9038
  address: 3496 Washington St

Coffee

• Fiore's Bakery

  phone: +1 617 524-9200
  address: 55 South St

• Ula Cafe

  phone: +1 617 524-7890
  address: 284 Amory St
  Local coffeeshop in the Sam Adams Brewery Complex which also serves breakfast and lunch, in addition to the usual coffee and pastries and some highly praised popovers. Free wifi connections available. Perfect to visit after the Sam Adams Brewery tour.

• Green T Coffee Shop

  phone: +1 617 487-8409
  address: 754 Huntington Ave

• 7 Pond Coffee Bar

  phone: +1 617 524-7663
  address: 7 Pond St
  High quality coffee, espresso, and pastries.

Still solidly residential neighborhoods, Jamaica Plain and Mission Hill have only one place to sleep each. Check your favorite room renting application, or start making friends now!

• EnVision Hotel

  phone: +1 617 383-5229
  address: 81 S Huntington Ave

• Taylor House Bed and Breakfast

  phone: +1 617 983-9334
  address: 50 Burroughs St

The two libraries here offer free wi-fi, supplementing the coffeeshops you'll find throughout the neighborhoods.

• Parker Hill Branch

  phone: +1 617 427-3820
  address: 1497 Tremont St

• Connolly Branch

  phone: +1 617 522-1960
  address: 433 Centre St

• It's a bit easier with a car, but check out the great views and some of the first cars ever built at Larz Anderson Park in Brookline.
• Speaking of Brookline, check out Fairsted. Every city has a park designed by Frederick Law Olmsted, but how many have the office (and grounds) he designed them from?
• Touring Franklin Park will technically place you in Roxbury, but this may come as news to some locals.
• Head north into Fenway/Kenmore to take in the Isabella Stewart Gardner Museum.
• If you're not tired of all that green space yet, check out Forest Hills Cemetery, also in Roslindale.