Boston/Roxbury

First settled by Europeans as an independent town in 1630, Roxbury was enormous and encompassed about half the neighborhoods in Boston today. Over time each area would incorporate and break off, until Roxbury itself was annexed to Boston in 1868. A particular type of stone, Roxbury Puddingstone, is found locally and outcroppings in the area are quite visible. Many notable buildings in town are constructed with this material. It may even be where the neighborhood gets its name, "Rocksberry".
Over the years Roxbury has absorbed waves of immigrants; after the English, the Irish arrived in the mid 1800s, followed next by Germans in the early 1900s. In the early 20th century a large Jewish population also moved into Roxbury. The most recent cultural changeover began in the 1940s and 50s, when an influx of new African American residents migrating from the south arrived alongside immigrants from the Caribbean.
Roughly, Roxbury can be divided into "upper" and "lower" halves, with Martin Luther King Boulevard serving as a dividing line. Heading south towards Franklin Park you'll notice a small change in elevation, which distinguishes the halves. Lower Roxbury was absolutely gutted during the 50s and 60s. The white flight to the suburbs began first, and when acres of city blocks were flattened by unfair urban renewal policies, few residents remained to speak up. Upper Roxbury remained largely intact, but the entire neighborhood suffered disinvestment and neglect by the rest of the city. You could understand why the community was ready to break away during the 70s and 80s. Instead of a new government, however, those who remained channeled their energy into setting up a new strategic development plan that would work for everyone.

Neighborhoods

• Dudley Square This is really the heart of Roxbury. Strategic plans dreamed up in the 1980s are finally coming to fruition as the city of Boston invests millions of dollars bringing back the Bolling building and other structures in the neighborhood. Longtime residents rub elbows with fresh arrivals taking advantage of the proximity to downtown, access to amenities, and the lower cost of living. With Bartlett Yard under construction and big plans in the works for other parcels, this area of town is viscerally experiencing gentrification.
• Egleston Square Is it part of Roxbury? Part of JP? This community at a crossroads is a great example of what Roxbury has to offer. A variety of shops and restaurants cater to the locals in the area, while many non-profits have taken root here. Investing in urban youth, here parents can find classes covering everything from baseball, to SAT prep, to creative writing and more.
• Fort Hill Set on a hill at the western border of Roxbury, Fort Hill is a quiet residential community. There are many interesting architectural gems dotted throughout the one way streets and hillsides just waiting to be discovered. Sometimes called "Highland Park", this neighborhood doesn't have much in the way of shopping and restaurants, but does contain a community college and a mosque.
• Grove Hall A mostly residential neighborhood largely made up of stately Second Empire and Victorian homes. Access to a bustling commercial district and close proximity to the enormous Franklin Park round this neighborhood out. No trains serve Grove Hall only buses, because of this fact many Bostonians don't even know this neighborhood exists!

By public transit

The Orange Line provides Roxbury with three busy stations located along the Southwest Corridor. Ruggles is by far the largest and has the most connections to local busses and the Commuter Rail. While Roxbury Crossing gets a lot of use from residents, and the nearby student population in Mission Hill. Further down the line Jackson Square is used by many residents of Egelston Square and Upper Roxbury. If you're headed to Franklin Park by train, consider staying on another stop or two to Stony Brook or Green.
Ruggles is also your stop if you're arriving from the suburbs. This is the only stop in Roxbury for the Providence, Franklin, and Needham Commuter Rail lines. It seems like almost every bus in the city winds up at Ruggles at one point or another. Popular routes include the #23 and #28 which run to Ashmont and Mattapan stations respectively. The CT2 and CT3 are part of the cities cross town loop system and will take you to either MIT or BU Medical. The #66 another helpful crosstown bus headed to Allston, can be picked up from the Roxbury Crossing station.
The beginning of the Silver Line can be found at Dudley Square Station in Dudley Square. This BRT route runs into downtown, to the airport and many other locations. The only other stop it makes in Roxbury is Melnea Cass Boulevard, before entering the South End. The station itself is a large bus depot, any route you missed at Ruggles can be picked up here.

By car

Driving in Roxbury is, like everywhere else in Boston, not recommended. It's only potentially worth the hassle if you're planning on heading to Franklin Park, or really getting off the beaten path. Parking is a little less competitive here than downtown, however, traffic can still back up quickly, and unpredictable driver behavior is common. Because of the hilly and rocky topography, streets here are laid out in an even less cohesive plan than other areas. Roxbury has more than its fair share of dead end streets and roads to nowhere.

• Franklin Park

  phone: +1 617 635-4505
  address: 1 Franklin Park Road
  The crown jewel in Frederick Law Olmstead's Emerald Necklace system of parks, Franklin Park brings together rural scenery, a woodland preserve, and areas for recreation and sports. Although funding for upkeep has been inconsistent over the years, the park's 485 acres provide thousands of city dwellers with unmatched green space. Take your time and investigate the old stone bridges and ruins scattered along the 15+ miles of rustic walking/hiking paths. Urban explorers shouldn't miss the Long Crouch Woods, site of Boston's first zoo. A grand staircase, deteriorating for a century, arcs up to reveal a long arcade lined with giant bear cages built of iron. If you're looking for a more focused undertaking, check out the entries for the golf course and modern zoo below.

• Highland Park

  phone: +1 617 635-4505
  address: Highland Park
  This site once contained earthwork fortifications built by the Continental Army during the Siege of Boston, and its clearly defendable location still offers sweeping views of downtown Boston. Fort Hill, the neighborhood's modern name, was inspired by these earthworks. The small park contains the Cochituate Standpipe, also known as Fort Hill Tower, built in 1869. It was once used to provide water pressure to area residents, but was only in use for a few decades. The tower makes a good point of reference when navigating Roxbury. Keep checking its location when you're worried about getting turned around.

• The Museum of the National Center of Afro American Artists

  phone: +1 617 442-8614
  address: 300 Walnut Ave
  This museum is dedicated to black visual arts heritage worldwide, and presents historical and contemporary exhibitions in many media, including painting, sculpture, graphics, photography and decorative arts. Although the organization's name specifies African American artists, it also includes examples of African diasporic art. The NCAAA is housed in the building Abbotsford, built in 1872 in the High Victorian Gothic style. The mansion was designed to evoke the fortified castles popular during the middle ages.

• Roxbury Heritage State Park

  phone: +1 617 445-3399
  address: 183 Roxbury street
  This heritage park is located in the John Eliot Square area of Roxbury, originally the center of town after its founding in 1630. The Dillaway-Thomas House here was built in the Georgian style during 1750 for the pastor of the First Church of Roxbury. Which still stands today just across the street. In April 1775, John Thomas, an American commander in the Continental Army, took possession of the house. Using it as a base of operations during the siege of Boston. By early March 1776, Henry Knox had transported cannons from Fort Ticonderoga in New York and through Roxbury, when Thomas led the charge to fortify Dorchester Heights. He and his men used the cannons to force the evacuation of the British from Boston on March 17. The house returned to the ownership of Pastors and Educators until was eventually purchased by the City of Boston in the 1920s, and slated for demolition. Activism by Roxbury residents saved the structure, and it began its current path to restoration in the 1930s.

• Shirley-Eustis House

  phone: +1 617 442-2275
  address: 33 Shirley St
  The house was built in 1747 as a summer home for William Shirley (1694–1771), Royal Governor of the Province of Massachusetts Bay. It is one of the last remaining mansions of royal governors in the United States. After the Revolutionary War, the home was seized as "Loyalist property" in 1778 and sat unoccupied for four years. For the next 100 years the home would pass through the hands of many wealthy Bostonians, Ambassadors, and Governors. Eventually it fell into being used as a tenement building, and in 1911 it was once again abandoned. Two years later, the founder of the Society for the Preservation of New England Antiquities took on a new role, and began the work of preserving the house. The structure was again extensively renovated during the 1980s. The work included an award winning restoration to the grounds, including an orchard, period perennial beds, parterre gardens, and a large formal lawn. Today it is used as a living museum, be sure to check the events calendar for what's new.

• Franklin Park Zoo

  phone: +1 617 541-5466
  address: 1 Franklin Park Rd
  Franklin Park Zoo, founded in 1912, is a 72-acre site nestled in Boston’s historic Franklin Park. This zoo contains a combined 10,000 sq ft of playground area and uses play to teach children about conservation and wildlife. In addition, it has an Australian bird aviary, a bird world's exhibit, an African lions exhibit, a tigers exhibit, a tropical forest environment, an outback trail, a butterfly tent, barn houses with farm animals, expansive giraffe and zebra savannah, a camel trek, a carousel, a train ride, a stationary jeep ride, picnic areas, a southwestern-themed grill concession stand, and a children's zoo!

• William J. Devine Golf Course

  phone: +1 617 265-4084
  address: 1 Circuit Dr

• Hibernian Hall

  phone: +1 617 541-3900
  address: 184 Dudley St

• 826 Boston

  phone: +1 617 442-5400
  address: 3035 Washington St
  Volunteer and teach the next generation of poets and writers. Also sells a variety of "Big Foot" souvenirs, alongside books by local authors.

• Morgan Memorial Goodwill Industries

  address: 1010 Harrison Ave
  This is the main distribution center for the other stores in the city, so it tends to have the biggest and best selection of donated items. Big parking lot and convenient drop off point for your unwanted items.

• Boston Gardener

  phone: +1 617 606-7065
  address: 2131 Washington St
  Friendly, knowledgeable staff can answer any question about what to do to with your soil. Complete selection of hydroponic supplies, lighting, and fertilizer. They also sell many smaller items like pots and seeds.

• Skippy White's Records

  phone: +1 617 524-4500
  address: 1971 Columbus Ave

• Tasty Burger

  phone: +1 617 425-4444
  address: 2200 Washington St

• Haley House Bakery Café

  phone: +1 617 445-0900
  address: 12 Dade St
  Community focused comfort food.

• Preparations

  phone: +1 617 445-5120
  address: 220 Columbia Rd
  Simple Caribbean fruit and vegetable market that also serves dynamite oxtail.

• Island Style

  phone: +1 617 288-8300
  address: 183 Washington St

• Ashur Restaurant

  phone: +1 617 427-0599
  address: 291 Roxbury St

• Suya Joint All African Cuisine

  phone: +1 617 939-0582
  address: 185 Dudley St
  Delicious Nigerian food in a lively environment, with the big-screen TV at the bar hooked up to YouTube and showing African hip-hop and R&B videos. The house specialty that gives the place its name could be described as an African version of Southeast Asian satay: appetizer-sized servings of skewered beef or chicken spiced to your liking. Main courses largely consist of a roster of Nigerian-style stews eaten with balls of fufu (this can be challenging for beginners; do your best). There's also a small range of Guinean and Sierra Leonean specialties for those who'd like to extend their exploration of African cuisine beyond Nigeria. Service is friendly if sometimes slow.

• Merengue Restaurant

  phone: +1 617 445-5403
  address: 160 Blue Hill Avenue

For a neighborhood of its size and population, Roxbury seems to have a dearth of drinking establishments. Don't worry, there are PLENTY more in neighboring areas.

• C & S Tavern

  phone: +1 617 442-7023
  address: 380 Warren St

• Bully Boy Distillers

  phone: +1 617 442-6000
  address: 35 Cedric St

• Biff's Lounge

  phone: +1 617 445-0324
  address: 24 Washington St

Coffee

• Dudley Cafe

  phone: +1 617 445-1000
  address: 15 Warren St

• Best Western Plus Boston Hotel

  phone: +1 617 989-1000
  address: 891 Massachusetts Ave

• Guild Street Townhouse

  address: 4 Guild St
  A vacation home on a quiet residential street that's available for weekly rentals. Sitting room with free flat-screen cable TV; balcony with view over the city; full kitchen with oven, microwave, dishwasher, dishes and silverware. Free WiFi. Free onsite parking.

The only coffee shop in Roxbury, true to form, offers free wi-fi facilities. These three BPL branches can also help you out in a pinch.

• Dudley Branch

  phone: +1 617 442-6186
  address: 65 Warren St

• Egleston Square Branch

  phone: +1 617 445-4340
  address: 2044 Columbus Ave

• Grove Hall Branch

  phone: +1 617 427-3337
  address: 41 Geneva Ave

• Like Franklin Park? Head west into Jamaica Plain and check out the Arnold Arboretum.
• Hop on the Silver Line and ride north into the shopping and dining destination the South End.
• Explore Roxbury's eastern border and try to figure out exactly where Dorchester begins and Roxbury ends.
• Investigate some of the quieter areas of town in the Outer Neighborhoods of Mattapan and Roslindale.
• Renowned museums like the MFA and Isabella Stewart Gardner are in Fenway/Kenmore, just across the Southwest Corridor Park.