Roadtrip Nation has meandered through most of the major cities in the US, and over the years we’ve accrued a lot of knowledge about where to go/eat/park a 35-foot vehicle. We like to think of ourselves as seasoned veterans of the road; sherpas of the pavement; stewards of turning down the absolute wrong street and stumbling upon an unreasonably delicious slice of pizza. We’ve logged over 10,000 miles on the road this summer alone, so after 15 years exploring the nation’s byways, here are our tips on what to do while you’re visiting Washington, D.C., New York City, San Francisco, and Chicago. Remember these spots the next time you plan a road trip!
City Guide: Washington, D.C.
1) Georgetown Cupcake: A delicious cupcake bakery founded by two sisters in DC (and featured on The Food Network), this is place where scarfing down one (or 3) frosting-topped mounds for breakfast won’t be frowned upon. Pro-trip: every morning, the bakery posts on their Twitter account about a secret flavor! If you’re one of the first 100 to request that flavor cupcake, you get it for free!
2) Try renting a bike! Capital Bikeshare is a company that rents out bikes at various stations throughout the city. We recommend picking one up for a requisite tour of the National Mall and monuments. Seeing all those sights by foot can be quite an endeavor, so it’s WAY easier and quicker to hop on one of these and roll around. These bikeshares are located all around town, and you can easily rent a bike at one station and return it to any other one that has an open spot.
3) Many of the monuments in DC are accessible/open all night long. Seeing them all lit up at night can be really special (plus it’s way less crowded in the evening).
4) Busboys and Poets is a historic restaurant founded by Andy Shallal in 2005 (you can check out our interview with Andy here). His mission for this restaurant was to have a gathering place for people of all different incomes, races, and identities to come together and exchange ideas about social and political issues. Today, Busboys and Poets remains a popular restaurant and community resource for artists, activists, writers, thinkers, and dreamers.
City Guide: New York City
1) Times Square is perhaps one of the most iconic areas of the city, and what tourists often imagine first when they think of NYC. What should you expect? Massive billboards, bright lights, and huge swarms of people! If you’re lucky, you’ll spot Robert Burck, a street performer we interviewed in 2007. He has been named by the New York State tourism department as “more recognizable than the Statue of Liberty.”
2) The High Line is a public park on the West Side of Manhattan. Built on a historic rail line, this park is free to the public and a great place to people watch/ picnic/ go for a stroll through some lovely gardens.
3) Visit the galleries in NYC’s Chelsea Neighborhood. Entrance is free, and you can see some spectacular exhibits! While you’re in the area, stop by Chelsea Market for a bite to eat. This urban market has something for everyone.
4) Looking for an inexpensive way to see the Statue of Liberty? Look no further than the Staten Island Ferry. Hop aboard (it’s free!) and you’ll get a great view of Lady Liberty. It also provides an interesting viewpoint from which to check out the NYC skyline.
5) The Meatball Shop: On our most recent road trip, we ate at The Meatball Shop four nights in a row. In a city with almost unlimited amounts of amazing cuisine, we just couldn’t quit this place. Give it a shot!
City Guide: San Francisco
1) Golden Gate Bridge: this is one of the world’s most iconic pieces of scenery. Need we say more? You can rent bikes near the bridge if you’re interested in taking a scenic ride across it.
2) Hog Island Oyster Company: You’re in San Francisco, so you’ve got to try some seafood, right? With good food and great views, we recommend that you check this place out!
3) Haight Ashbury: This area is known for being a hub for the hippie movement in the 60s- the neighborhood was the home for the Summer of Love in 1967. Go to Haight Ashbury to soak in some American counterculture history!
4) Bi-Rite Creamery is possibly some of the best ice cream that we’ve tasted in the country. Smooth creaminess and wonderful flavor combinations will make your taste buds sing.
5) There are few better ways to see the city than jumping on a trolley. While we typically recommend sightseeing in an RV, this is a great San Franciscan alternative. Hop on board and see the sights via this cool, old-school public transportation system.
City Guide: Chicago
1) You basically haven’t visited Chicago unless you’ve tried deep dish pizza. We recommend either Giordano’s and Lou Malnati’s.
2) Millenium Park: You have to visit Millenium Park, if for no other reason than to get one of those goofy pictures of your reflection in Cloud Gate (also known as “The Bean”), a towering mirrored sculpture installation by Anish Kapoor. Located in the heart of downtown Chicago, this site has become iconic and was practically engineered for selflies. Plus, if you time it right, there are free symphonic concerts in the summer at an amphitheater in the park!
3) The Willis (Sears) Tower is the highest skyscraper in Chicago, and has an observation deck that’s not for the faint of heart. “The ledge” is a glass balcony where you can stand and take in the impressive view (from 1353 feet off the ground). Beware- those afraid of heights will not be fans.
4) Don’t miss Grant Park, a stretch of green space located downtown. It’s a great place to check out public art, the iconic Buckingham Fountain, and beautiful gardens. Love live music? The Lollapalooza music festival takes over Grant Park every summer!
Check out these spots on your next road trip!