Last Updated on June 3, 2025 by Steph
We spend many weekend days strolling in the city. I like to refer to it as “urban hiking” because it’s all about the exploration. We rarely have an agenda; we just wander. It’s an easy way to get outside and enjoy a beautiful day, and also get some exercise. The best part about this method is finding all the secret dive bars and awesome food trucks that don’t hang out near your regular routes. In New York City? Check out our favorite neighborhood, Clinton Hill, for some great scrollable streets.
Comfort is key when we are strolling, so here are some of the basics we require for a good Sunday (or any day) stroll.
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Urban Hiking Essentials for Men:
Adjustable trucker hat like the Billabong hat pictured. It helps keep the sun out of your eyes and the wind from messing up your hair (for those who care.)
A classic backpack. We love the colors and styles of the Herschel Supply Co. This is important if you plan to stop in any record shops or farmers markets or maybe a candy store – it can hold your goodies that you pick up along the way.
Comfortable t-shirts. Our favorites are from Marine Layer, but anything you love will work.
Good walking shoes. Justin’s favorite is Merrells, but anything that allows you to walk a few miles without foot pain is essential. If you do experience foot pain, that’s when you should stop for a snack or an ice-cold beverage.
Urban Hiking Essentials for Women:
Sunglasses. Wayfarers are my jam, but everyone has a style they love. Just don’t forget them.
Classic jeans + t-shirt look. It’s comfortable, you can wear it to most places, and you just really can’t go wrong. I love all the t-shirts found on this website, and the jeans are just plain old Gap – never fails me.
Tote bag. I like to have something that I can store any souvenirs or books from Little Free Libraries, plus sunscreen and a water bottle.
Great shoes. I used to be a fan of Toms for everything, but lately, I’ve been wearing my Nikes everywhere and have them in three different colors.
Additional Urban Hiking Essentials:
Public transportation tickets. If your feet end up hurting too much, you’ll need a way to get home. We love jumping on the subway, even to just get to a new neighborhood. Most cities in the US have bike share or public transportation to use – try it!
Apple Watch or a step tracker. We both have the series 10 and love them. On strolls in the city, we average about 8,000 steps.
Water bottle and/or coffee thermos. Our household is hardcore Owala fans. We own four, so we can rotate with a good cleaning schedule. It’s essential to bring water with you. We sometimes take a to-go coffee from our apartment before heading out in the morning (and then refill as we go.)
A Camera. We have multiple cameras for different adventures, but nothing is as fun as the Instax we got last year. It’s fun to leave people with souvenirs of your shared lunches or adventures, or just snap a few colorful shots. We’ve also been loving the disposable cameras, as they encourage us to use our phones less and less.
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So that’s the basics. Get out there and explore your city.
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