Northwest Philadelphia includes Germantown, Mount Airy, and Chestnut Hill, all of which run along Germantown Avenue, the east–west divider. The easiest way to get to this area from downtown is to take Kelly Drive, Martin Luther King Boulevard (formerly West River Drive), or the Schuylkill Expressway and either take Lincoln Drive or head east through East Falls on Midvale Avenue or Schoolhouse Lane to the Germantown area.

Be warned that these roads are subject to wind, and locals sometimes treat them as speedways. Manayunk is just down the river from East Falls, about a 10-minute drive from the Philadelphia Museum of Art. Going north along Germantown Avenue, Germantown becomes Mount Airy (somewhat fuzzy dividing line) and then becomes Chestnut Hill at Cresheim Valley Drive. Valley Green, an extension of Fairmount Park and Wissahicken Park, divides Mount Airy and Chestnut Hill from the Roxborough, Andorra, and Manayunk sections of the city.

Main Street in Manayunk is like a vacation village, with boutiques, sports bars, and restaurants. Sitting along the Schuylkill River, the rest of the neighborhood rises steeply up the hill, with houses crammed together up twisting streets.

Nearly all of the area's 18th-century homes are located in Germantown, most of which are along Germantown Avenue, which is alternately historic and ramshackle. There are a lot of beautiful residential houses in the area, but it's not a suitable place to wander alone at night.

Chestnut Hill is Philadelphia's most relaxed neighborhood as well as one of its greenest. People gather here to eat and wander about the precious shops on Germantown Avenue. It's a great neighborhood for peering into people's homes as well. Mount Airy has seen an increase in dining, drinking, and shopping establishments. Although its businesses are less concentrated than in Chestnut Hill, there are a number of hidden corners with charming cafés, and some great beer at Earth Bread and Brewery.