South Brookline - Chestnut Hill, MA

Eighteenth century South Brookline was a community of farmers and dignitaries trying to make a living in a very young New England. Even in those early days, the area lured wealthy businessmen from nearby Boston. Strong conservation laws kept many of those original estates intact and ensured today's South Brookline has a spacious feel. Among those original landholdings are a working farm, a cemetery, and a convent. Not surprisingly, South Brookline claims the country's first country club, opened in 1882 in Clyde Park. The club was originally intended for horse racing, but later housed mixed-sports entertainment, setting precedent for country clubs across the country.

The Brookline Historical Society, a local non-profit organization dedicated to preserving and educating around the area's rich past, provides locals and visitors an in-depth view of South Brookline through the years.

The Brookline Arts Center provides a place where individuals feel free to express themselves through art. The Center hosts an annual Snowflake festival where community members celebrate and participate in the creation of art. The event includes free art workshops, with creations displayed in the Center's gallery.

South Brookline has no shortage of fine dining. The restaurants of Putterham Circle, the roundabout connecting Grove Street and West Roxbury Parkway, provide residents with a local night out. Mandarin Gourmet, the area's premiere Chinese eatery, features traditional Mandarin and Szechuan dishes in a family-friendly setting. Customers choose from American Chinese staples like crab rangoon and egg rolls to more unusual specialties like scallops in wine sauces. Health-conscious eaters love the low calorie specials, free of MSG, salt, cornstarch or sugar. Budget-minded diners like Mandarin Gourmet's lunch menu which features specials priced below $10 every day of the week.

A few doors down on West Roxbury Parkway lies another local favorite, Putterham Grille. This Brookline staple serves a perfect balance of homemade classics and internationally inspired dishes. Appetizers include the mezze plate, a healthy sample platter of house tzatziki, hummus, and kalamata olives. For soups, customers choose from homemade chicken noodles, matzo ball, or the soup du jour. The lunch menu tends towards big open-faced deli favorites like the brisket or reuben, while dinner entrees feature choice cuts of steak and classic pastas. Either way, diners need to save room for one of the signature desserts like the ricotta pie topped with amaretto reduction and fresh strawberries. Residents typically head into Boston proper for a night on the town.

The proximity to downtown Boston makes South Brookline an ideal location for urban professionals. A 20-minute drive down highway MA-28 ends in downtown Boston, where drivers can brave the street parking or opt for one of the city's many parking garages. To avoid the hastle of parking, the 51 bus is an economical and environmentally friendly alternative mode of transportation. This route runs along Grove Street, bringing riders to the subway's orange and green lines to catch a lift to other points of the city. Given the neighborhood's residential nature, taxi service is difficult to pick up on the street, but reservations are available through any of Boston's taxi providers. Uber provides a popular ride sharing option.

South Brookline lacks dedicated bike lanes, yet bikers find neighborhood streets relatively low-traffic. Bikers heading east towards Jamaica Plain ride along the bike-friendly VFW Parkway, which eventually connects to equally bike-friendly Centre Street, a major hub for restaurants and shopping. Within South Brookline, the winding roads and large estates make for ideal neighborhood jogging in a semi-rural setting.

In keeping with its rural feel, South Brookline has many good options when it comes to parks. Hancock Woods invites visitors to explore its wooded trails, home to many varieties of Oak, Sweet Birch, and Sassafras trees.

On the east side of the neighborhood lies Walnut Hills Cemetery, a historically significant burial ground spanning more than 45 acres. Many of the town's prominent citizens are buried here, including H. H. Richardson, a noted 19th Century architect.

North of the neighborhood lies two sprawling golf courses, Putterham Meadow, and Robert T. Lynch Municipal. The latter was constructed in 1933, and has since grown with new land acquisition. Together, these courses provide local residents with outdoor recreation in a pastoral landscape.

While many of Boston's suburbs offer a family-friendly setting outside the city, few compare with the combination of rich history, excellent public schools, and open space that South Brookline provides. When it comes to rental properties, South Brookline remains significantly lower than Boston proper. The median one-bedroom in South Brookline goes for $1,673 a month compared to $2,350 per month within Boston's city limits. The lower price and abundance of single family homes means rental properties are scarce in South Brookline. For commuters, the Mass Bay Transit Authority offers bus passes at $50 a month, or $75 a month to include subway access. Individual rides are $2.10 for the bus and $2.65 for subway, with both offered at a discount when using the CharlieCard, the eco-friendly MBTA rider card. Massachusetts gas prices are only slightly below the national average. The state's blue laws prohibit discounting alcohol sales, resulting in some creative food discounts to make up for the traditional happy hour among local bars. A cold beer typically goes for around $4-$6 for domestics.

Located at the intersection of West Roxbury Drive, Independence Drive and Grove Street, The Shops at Putterham is South Brookline's alternative to a standard suburban mall. Shoppers drop off the dry cleaning with Towne Cleaners and then head to Brookline Bank, a neighborhood full-service bank serving Brookline residents since 1871. Avery & Co. is a gift shop that features stationery, kitchen gadgets and lotions for the bath.

While the Shops at Putterham provide a one-stop shop for South Brookline locals, no other store draws a wider customer base than Cheryl Ann's Bakery. Anyone who's ever been to a Boston Area shabbat dinner has likely tasted a loaf of Cheryl Ann's famous challah, the braided Jewish sweet bread typically eaten on Friday nights to mark the Sabbath.

Cheryl Ann's challah is not only for shabbat, it makes an other-worldy French toast. Beyond the famous challah, the bakery churns out a range of other Old World classics like turnovers, bubkie, rugalah, and hamantaschen, the triangular shaped Purim holiday favorite filled with a choice of chocolate, several fruit spreads, or the classic poppy seed. Founded by sisters Cheryl and Ann in 1985, this South Brookline institution is an essential stop for people with a sweet tooth.