Best Road Trips Near Major U.S. Cities for Car Lovers

There’s something special about hitting the open road—windows down, music up, and miles of highway ahead. Whether you drive a sports car, a lifted truck, or a tuned sedan, the U.S. is full of short road trips that feel like a full escape.

No cross-country planning required, just a tank of gas and the will to roll.

Here are some of the best road trips near major U.S. cities for car lovers, handpicked for their scenery, fun roads, and unforgettable stops.

1. Los Angeles → Angeles Crest Highway (CA-2)

Distance: 66 miles round-trip
Twisty mountain curves, pine forests, and elevation changes, Angeles Crest is a favorite among car enthusiasts. You’ll find scenic pull-offs and views that feel a world away from the city. Just watch for cyclists and speed traps.

Why you’ll love it: Tight turns, cool air, and a chance to really feel your car on the road.

2. New York City → Bear Mountain & Seven Lakes Drive

Distance: 90 miles round-trip
Once you escape NYC traffic, this route takes you through the Hudson Valley and into one of the Northeast’s most underrated driving roads. Tree tunnels, lakeside views, and just enough curves to make it fun.

Why you’ll love it: Fall colors, vintage diners, and plenty of Instagrammable moments.

3. Miami → Overseas Highway to Key West

Distance: 330 miles round-trip
Ocean on both sides, long bridges, island vibes, the US-1 to Key West is pure magic. It’s not about speed here, it’s about enjoying the view and stopping for Cuban coffee or a slice of key lime pie.

Why you’ll love it: There’s literally nowhere else like it in the U.S.

4. Dallas → Hill Country Wine Trail (Fredericksburg)

Distance: 300 miles round-trip
Rolling hills, German-influenced towns, and great wine. Central Texas offers an unexpected combo of beautiful driving roads and laid-back charm. Ideal for a weekend getaway with good music and even better BBQ.

Why you’ll love it: Scenic roads and roadside gems that keep the vibe relaxed and fun.

5. Chicago → Lake Geneva, Wisconsin

Distance: 160 miles round-trip
Escape the Windy City and cruise through charming Midwestern towns up to this lakefront destination. Great for a quick romantic weekend or just an excuse to stretch your wheels.

Why you’ll love it: Smooth roads, relaxing stops, and that small-town charm.

Pro Tip: Protect Your Ride Before You Go
Road trips are epic, until something unexpected happens. Whether it’s theft, damage, or getting lost in the middle of nowhere, make sure your car is protected.

With VG Motors’ Ultimate Car Safety Package (LoJack + Decoy + 4K Dashcam + Faraday Bags), you’ll hit the road with peace of mind, and come back with only the good stories.