Twenty-five years ago this week, I was embarking upon what was at that time the most epic roadtrip I’d ever made. My friend Jeff and I ventured northward to New York and ultimately to Boston on a on-week urban odyssey that in many ways changed the way I looked at life and was the start of my urban transformation. Thinking about that trip as I plan a more modest one for this weekend, I decided it was time for a “top five best and most life-changing road trips ever” list. And here they are in chronological order:

New York and Boston (August 1988)

This is the trip outlined above. Jeff and I left in the evening, stopped outside Richmond, and arrived in New York the next day for three or four days at the Hotel Chelsea, which was at the time a quite inexpensive and wonderful option. Then we did three or four more nights in Boston with my friend Margo, after which we drove home with an overnight stop in DC.

Significant aspects:

This was my first non-family trip to New York so it was my first crack at urban nightlife. It was also the trip that made me realize I was a thoroughly urban sort and that my current home in Charlotte didn’t qualify.

Highlights and strong memories:

• The pre-gentrification Hotel Chelsea.
• The Tompkins Square Riots and the way we didn’t quite “get” what was going on at the time.
• My first encounter with the Cross-Bronx Expressway, which was to become something of an obsession in later years.
• Stifling heat in both cities and the way Jeff and I went to the drugstore and bought my college kid pals in Boston a fan because it had apparently never occurred to them to do so.
• A very long, drunk conversation with a male prostitute in the Boston Ramrod.
• The Pyramid Club, King Tut’s Wa-wa Hut, Ground Zero, Axis/DV8…
• “Peek-a-Boo” by Siouxsie and the Banshees playing everywhere.

San Francisco, Los Angeles, and San Diego (July/August 1991)

A two-week trip to visit friends on the West Coast resulted in my first quick visit to Los Angeles, a place with which my lifelong obsession was just beginning and in a surprising appreciation for San Francisco. I spent several days with Steve and Todd in SF, drove south to San Diego to see Stan for a few days, and then came back to SF for a few more days.

Significant aspects:

This is the trip that resulted in my move to the West Coast a year later and my decision to move to San Francisco rather that Los Angeles, which had been the plan up to that point.

Highlights and strong memories:

• My first ever (and last ever) trip to a bathhouse in San Diego.
• The Dore Alley Fair.
• The Market Street Safeway in San Francisco. And the Cala Foods at Hyde and California.
• Jack in the Box.
• Queer Nation T-shirts.
• The Detour, the End-up, the Overpass, some bar in San Diego whose name escapes me.

Planet SOMA US Tour (September/October 1997)

Well-documented itinerary. This was a five-week trip with real-time online updates from the road (no small trick in 1997) and accommodations with random strangers who were fans f what this website used to be.

Significant aspects:

This was sort of “web history” for me but more importantly it also signaled the beginning of the end of my monogamous relationship with San Francisco. I began to realize there was a whole country out there that was in most ways the equal (or better) of Sodom by the Bay.

Highlights and strong memories:

• My first look at Detroit after a several-year fascination.
• Walking into a Windsor bar and seeing very naked strippers on the tables.
• Flat tire in Gallup.
• Dad’s kidney stone.
• Going unexpectedly batshit crazy over Pittsburgh.
• Mark’s Powerbook.

Seattle and Portland (April 2002)

About three days in Portland and four days in Seattle with my new boyfriend Mark. Since my first visit at age ten, I’ve never been able to get enough of Seattle and still long to visit again.

Significant aspects:

This was Mark’s and my test drive for cohabitation. We also made some semi-serious plans to relocate to the Northwest afterward.

Highlights and strong memories:

• Beth’s Cafe.
• The fucking Fremont Troll that we were never able to find.
• A moderately embarrassing late-night trip to Walgreens in Seattle.
• A very exhausted and late dinner in Redding.
• Underground Seattle.
• Powell’s Books in Portland.

Toronto and Ottawa (October 2011)

Four nights in Toronto and four more in Ottawa, as I recall, with stops in Cleveland, Buffalo, and Schenectady. I visited Sarah and Brad in Buffalo, Robin in Ottawa, and Duncan and Rick in Schenectady.

Significant aspects:

This was really one of my favorite trips of all time. It was my first big vacation after splitting with Mark and the last one before all the drama with my parents. I fell (more) in love with Canada, communed with urbanity in a way I hadn’t in years, and became obsessed with francophone alt-rock.

Highlights and strong memories:

• Quatre-vingt-seize-cinq: Capitale Rock!
• Beef on Weck.
• Kensington Market.
• Poutine in Gatineau.
• Queen Street West. All of it.
• CBC Broadcast Centre.
• Unnecessary Canadian immigration paranoia.

Honorable mentions:

• Cross-country Move (September/October 1992)
  Hard to beat this one for “life changing” and as my first introduction to…well…the whole middle of the country. Funniest memory: Ditching a boy in a Kansas City bar only to run into him again four nights later in Salt Lake City.
• Chicago, Detroit, Toronto, and Pittsburgh (October 2006)
  Maybe the most urban vacation ever, with Mark. We were both sick in Toronto. I was impressed that this didn’t sour me on the place. Toronto is a wonderful place.
• Los Angeles and San Diego (July 2012)
  Following ALA, I was able to spend significant time alone in SoCal for the first time ever. It was heavenly. The fact that this was my first ever trip to California that in no way involved San Francisco had a certain charm as well. Great trip. Perfect timing.