Side-Questing 101: How to Discover Hidden Gems in Any City or Town

By Questly Team · 2025-01-18 · 10 min read

Every city has two versions of itself: the one in the guidebook and the one that locals actually live. The first version has the famous restaurants, the obligatory museums, and the well-documented attractions. The second version has the alley garden someone has been tending for 20 years, the taqueria with no English sign that serves transcendent food, the park that looks ordinary on a map but turns out to be full of deer at dusk. Getting from the first version to the second one is what we call side-questing — and it is a learnable skill.

Start With Curiosity, Not a Checklist

The most important shift in side-questing is moving from a checklist mindset to a curiosity mindset. A checklist says: I will see the five famous things and then I will have "done" this city. A curiosity mindset says: I wonder what is down that street. I wonder why this neighborhood smells like fresh bread at 6 a.m. I wonder what that building used to be. Curiosity-driven exploration is inefficient by the standards of tourist planning and enormously rewarding by the standards of actual experience. You will spend more time in fewer places and understand those places far more deeply.

Walk Slower Than You Think You Should

This is the most consistently underrated piece of advice in travel writing. Almost every interesting discovery in a city comes from walking slowly enough to notice things. Walking slowly means you can read the faded sign above the shop door, notice the small garden behind the fence, hear the music coming from the open window, see the old photograph in the barbershop window that tells the story of the block. Slow walking also makes you approachable — people are far more likely to stop and talk to someone strolling than to someone striding purposefully to their next destination.

Talk to People Who Work Outdoors

If you want to know the hidden character of a neighborhood, talk to the people who spend their days in it at street level: the mail carrier, the parking attendant, the person sweeping in front of the shop, the groundskeeper at the park, the food truck operator who has been in the same spot for 15 years. These are the people who have watched the neighborhood change and stayed. They know which building has the best rooftop view, which park has the deer, which restaurant owners cook the food they actually eat at home. This kind of knowledge cannot be Googled.

Use the Right Digital Tools (and Know When to Ignore Them)

Certain digital tools genuinely help in finding non-obvious places. Google Maps satellite view lets you spot parks, trails, and natural features that are not well documented online. AllTrails has user-submitted reviews of hiking trails that often include notes about wildlife, seasonal conditions, and off-trail features. iNaturalist lets you see what plants and animals other people have observed in specific locations, which is an excellent proxy for ecological richness. Old maps and historic aerial photography (available through county tax office websites and the USGS Earth Explorer) show you what was there before development and sometimes reveal the logic behind how a place is laid out.

Notice the Ordinary Things

The most reliable path to extraordinary discoveries is paying attention to ordinary things with more care than usual. The most interesting alley is never labeled. The most beautiful view is rarely at the official overlook — it is around the corner from the official overlook, through a gap in the vegetation, from a specific bench that angles just right. The most memorable meal is usually in the restaurant where the regulars are, not the one with the best online reviews. Pay attention to where locals are going, what they are eating, where they are sitting. They have already done the research.

Keep Notes (and Share What You Find)

The single most useful habit of experienced explorers is writing things down. The specific intersection where the live oak arch is perfect in the morning light. The name of the tamalera who sells from a cooler on Saturday mornings. The trail that leads to the swimming hole that is not on any map. These things are immediately memorable and quickly forgotten without a note. Physical notes, voice memos, or apps like Questly work equally well. The act of recording forces you to be specific about what you found and why it was worth finding, which sharpens your observational skills over time.