This post may contain affiliate links. When you make a purchase through these links, you’re supporting the creation of content here on the blog, at no extra cost to you. Thank you for your support.
📌 Love these ideas? Save this post on Pinterest to come back to it anytime!
Iconic destinations to include
26. Drive across the Golden Gate Bridge
Snap a photo as you cruise through San Francisco’s most famous landmark.
27. Visit Cadillac Ranch in Texas
Spray paint your mark on the famous half-buried cars in Amarillo.
28. Cruise the Pacific Coast Highway
Breathtaking ocean views, cliffs, and retro beach towns await.
29. Explore old ghost towns
Walk through deserted buildings and get a taste of the Old West.
30. Stop at the Blue Swallow Motel in New Mexico
One of the most iconic Route 66 stops with serious vintage appeal.
Unique roadside shops
31. Browse an old-fashioned general store
From glass-bottled sodas to handmade goods, it’s a treasure hunt.
32. Visit a retro gas station
Snap photos and enjoy the nostalgia of vintage fuel pumps and signs.
33. Shop at a vintage thrift store
Score retro outfits, records, and quirky souvenirs.
34. Find a kitschy gift shop
Look for those “I Survived” mugs, fridge magnets, and bumper stickers.
35. Grab a comic book or vinyl record
Look for hidden gems in dusty shelves or record bins.
Photo moments to remember
36. Pose with a classic convertible
Even if it’s not yours, snap a cute photo if you see one parked nearby.
37. Recreate an old family road trip photo
Bring along an old album and strike the same pose today.
38. Take mirror selfies at gas stations
The backdrop might be boring, but your outfit and smile make it golden.
39. Snap a pic with a motel sign
The funkier the font, the better the photo.
40. Capture sunsets through your rearview mirror
It’s a small detail that feels so poetic on the road.
Music and entertainment
41. Make a cassette-style playlist
Name it, decorate a case for it (even if digital), and treat it like a mix tape.
42. Play car karaoke
Turn up the volume and sing at the top of your lungs with the windows down.
43. Listen to a retro-themed podcast
Find a show about old Hollywood, vintage pop culture, or classic Americana.
44. Have a “no screens” hour
Put the phone away and enjoy the view like it’s the 70s.
45. Play 20 Questions or I Spy
Simple, nostalgic games that make the miles fly by.
Local adventures
46. Stop at a roadside carnival
Rides, cotton candy, and vintage signage—yes, please!
47. Visit a county fair
Check the calendar and see if there’s one along your route.
48. Explore an antique mall
You never know what treasures you’ll find for your home or closet.
49. Take a mural photo walk
Lots of small towns are full of painted walls begging for a photo op.
50. Find a local museum
Whether it’s weird, wacky, or wonderful—small-town museums are a treat.
Still going strong? 💡
There’s more roadside magic ahead — keep exploring for that golden-hour glow!
🍟 📼 ⛽
