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Drive Out of Your Comfort Zone: Road Trip Through the Mid-Atlantic

Travel Tips | Jim Werner | September 18, 2025

Ready to ghost your city stresses for a while? This month, we’re hitting the road. Grab your friends, get in the car, and take the scenic route with us as we uncover brilliant little stops and hidden surprises. We’ve got all the tips to make your road trip experience absolutely fabulous. What’s your all-time favorite road trip? Spill the tea! This time we’re going on a Mid-Atlantic fall road trip.

Believe it or not, fall is officially here. It’s time to trade those hot, steamy summer nights for crisp, colorful days and cozy evenings. While your beach memories and tan lines are still fresh, you’re probably ready for vineyard tours, bonfires, and foliage drives with that special someone. Now is the perfect time to plan a long weekend (or a full week—you deserve it!) to explore a gay-friendly city and its stunning countryside.

Your Destination: Southeastern Pennsylvania

We’re focusing on Philadelphia, Bucks County, New Hope, and Kennett Square—a region packed with autumn charm.

Getting There:

  • From New York and North: New Englanders, you’ll take I-95 South.
  • From DC and South: Just do the opposite and head up I-95 North. It’s not rocket science.

The Itinerary:

Get ready for a kaleidoscope of autumn colors and activities in the mid-Atlantic. Philadelphia and its surrounding countryside host fantastic fall festivals almost every weekend.

First up, Philadelphia throws the East Coast’s biggest National Coming Out Day celebration with OurFest (October 11-12). It’s a massive block party in the heart of the Gayborhood, complete with drag shows, games, bar crawls, and shopping.

Once you’ve had your city fix, head to the countryside where couples will find plenty of excuses for hand-holding.

If you’re feeling dramatic, you can stage your own version of The Bridges of Bucks County by discovering the 12 historic covered bridges scattered throughout this scenic part of the Keystone State. For the more athletically inclined, rent bikes and ride along the peaceful Delaware River Canal to soak in all the reds, oranges, and yellows.

While in Bucks County, a visit to the artist colony of New Hope is a must. Pop in and out of the funky shops, galleries, restaurants, and bars along its lively Main Street. To truly immerse yourself in this suburban oasis, book a night or two at a quaint, gay-friendly B&B.

Longwood Gardens fountains with trimmed hedges and sprays of water on a sunny day in Chester County, a highlight of a Mid-Atlantic fall road trip.

Also near Philly is Chester County’s Longwood Gardens—basically, the Madonna of gardens. It’s iconic and always reinventing itself. You could easily spend an entire day strolling through the sprawling gardens, exploring the conservatory, and admiring the famous dancing fountains.

No matter where your trip takes you, don’t forget to pack your camera and your comfiest PJs. After all, a Mid-Atlantic fall road trip provides the perfect backdrop for a new profile pic and, more importantly, plenty of cuddling.

RELATED LINKS:

Staying Fit While on the Road

Skip the Chips and Dip for These Healthiest Road Trip Snacks

Hit the Road, Jack: Road Trip Through Midwest

Find Healthy Food on Your Road Trip (There’s an App for That)

Drive Out of Your Comfort Zone: If Dolly Can do It, So Can We!

Hit the Road, Jack: Making a Run from the Border to the Desert

Hit the Road, Jack: California Colors

Drive Out of Your Comfort Zone: Road Trip Through New England

Drive Out of Your Comfort Zone: Road Trip Through Northern California

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And let’s be honest, that’s pretty darn gay.
 

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