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Squirrel Hill to Oakland and Back

Pittsburgh, Pennsylvania , United States
4.7 mi




ft elev +


Your adventure will start at the Beacon St + Murray Ave station, in the heart of Squirrel Hill. This neighborhood is notable for being an important Jewish cultural center within Pittsburgh. It is also a popular neighborhood for students from Oakland to visit. It’s a thriving hub that includes restaurants featuring cuisine from all over the world, theaters, a library, and many local shops. This route will take you past businesses, parks, and Phipps Conservatory. Start heading West on Beacon St until you reach Wightman St. Cycling up this slope will warm your body up. After that, enjoy a nice breeze as you gain speed effortlessly while going downhill. Turn right onto Wightman St. Continue on until you reach Darlington Rd. Here you will be able to relax and enjoy the shade from the beautiful trees on this street as you put the dedicated bike lane to good use. We recommend turning left onto Darlington Rd. Remember to use your hands to signal a left turn so that any car behind you knows your next step. If you prefer, you can dismount from your bike and use the crosswalk. Once you are on Darlington Rd, your ride will be downhill half of this road. This will allow you to take a look at the different houses in the neighborhood. At some point you will encounter a little slope. Remember to shift your bike’s gear to ease your pedaling. As soon as you reach the intersection, turn right to stay on Darlington Rd. Continue on Darlington St until you reach Schenley Dr., then turn left onto Schenley Dr.
Turn left onto Schenley Dr., and use the shoulder to cruise between green grass and golf courses. This street goes through Schenley Park. When you reach Tech St, you will see Carnegie Mellon University on your right. After going down on Schenley Dr. for a little bit, you will have the option to make a quick stop to check The Westinghouse Memorial, which is a bronze monument that commemorates George Westinghouse, an engineer and inventor of the railway air brake.
After a short rest, return to the route and head to The Phipps Conservatory. Use the crosswalk to access the protected bike lane. Here you can do another quick stop and smell the colorful flowers by the main entrance.
Jump back on your bike and resume your ride. You will see the main branch of the Carnegie Library of Pittsburgh, the Mary Schenley Memorial Fountain, and Schenley Plaza. Now that you have reached Roberto Clemente Dr., continue straight and turn right onto Bouquet St. Congrats! You made it to the Bouquet St + Sennott St station. If this is your final stop on a Healthy Ride for the day, make sure you return your bike to the station. Oakland has a lot of good food options! Get some bubble tea and relax at Schenley Plaza. If you are planning on heading back to Squirrel Hill, you will take the same route back. The only difference is that after you go past the golf course at Schenley Park, you will keep going straight on Forbes Ave. for a little bit before turning right onto the dedicated bike lane on Wightman St. We hope you enjoyed this ride as much as we did!