If I had a nickel for every time someone asked me to tell them the best place I’ve ever been, I’d be picking up the check at happy hour more often.

I understand the appeal of asking a travel writer this question, but good-God do I dread it. Not because I think it’s a stupid question – as I said, I get it – it’s just that visiting these four towns in such a short time drove home the point that destinations are different, and that while comparisons are understandable, rankings can be counterproductive when they don’t tell the whole story.

Other travel writers I’ve met have advised me to shoot from the hip. They said they answer this question differently almost every time, depending on their mood or where they’ve been recently. I adopted this method almost religiously in the beginning, spouting off names like Barcelona and the Exuma Islands, but I have since resorted to analogies in an attempt to explain why I can’t truthfully answer the inquiry, how the type of trip you’re going for really changes the answer.

I don’t go to Hawaii to snowshoe, Quebec City to sunbathe, or the Bahamas for fine dining. Each place has something that makes it unique and other things that it lacks, and I hate the school of thought that says since two places are different, one must be better and one must be worse. That’s not how I live my life, and it’s certainly not how I go about my business as a travel writer. To steal a thought from the Tao: When something is labeled as beautiful, ugliness is created.

That’s why when we start handing out awards, I think they need to be done so very specifically. What’s better? A three-day tequila binge in Cabo or a three-day wine tasting tour of Napa? I don’t know, you tell me. What kind of mood are you in? “Top Ten Bars in the World” sells and sounds sexy, but what the hell are we talking about? How is an ice bar in Sweden better or worse than a floating bar in the Caribbean or a salty dog along the coast of Key West?

Which makes this final post of the Coolest Road Trip so difficult – I feel like I’m comparing apples to oranges in even attempting to categorize them. It’s one thing to contrast similar fruit – like discussing your favorite happy hour spots of the year or why you prefer one beachfront hotel over another – but how am I supposed to pick winners when comparing a Victorian beach town, an Appalachian Trail mountain town, an Outer Banks maritime boating town, and a wine-infused lakeside community?

Wish me luck – here goes nothing. As my explanations will show, it’s not only the music, it’s how and when you hear it.

Coolest Accommodations: Damascus Cabins, Damascus

Why: I arrived in Damascus a weary traveler, having worn myself out on nightlife in Beaufort the previous three nights. The cabin’s location next to the river made it a peaceful place to regroup. As I wrote earlier, people visit Damascus to escape it all, to lose themselves in the wilderness, and the cabin fit that agenda perfectly. I didn’t have to deal with hotel staff or find a place to eat. I made myself a drink, grilled out, and watched the lightening bugs. Sit by the campfire after dark to get the full experience.

Coolest Place for Happy Hour: Rhum Bar, Beaufort

Why: This selection should come as no surprise to anyone who has followed this blog, specifically the discussion of my five most memorable happy hour experiences of 2011 (three of the five occurred in the Caribbean). There’s something about that island vibe, and I’m fully convinced that the late afternoon hours should be dedicated to it. Read what I had to say about Rhum Bar in a previous post.

Coolest Restaurant: Mad Batter, Cape May

Why: Every morning feels like Sunday morning in Cape May, a town that doesn’t really wake up until 10 a.m. My crab Benedict was solid and the bar is a popular happy hour spot, but it is the brunch vibe that sets the tone for the entire day. Hit the Mad Batter for a few mimosas on the way down to the beach, and then for a casual happy hour on your way back.

Coolest Outdoor Activity: Hot Air Balloon, Hammondsport

Why: If I hadn’t made a rule before this began that nothing could win two categories, my ride in a hot air balloon over Lake Keuka in Hammondsport would have also won the Coolest View award. Simply a spectacular adventure – read about it and see photos here.

Coolest Historical Aspect: The Legend of Blackbeard, Beaufort

Why: Hard to believe those pesky pirates still plague our world today. Check out stories of one of the most infamous, Blackbeard, who lived in Beaufort before he was captured and beheaded.

Coolest View: Parasailing, Cape May and Beaufort

Why: Parasailing may not be the most exciting thing in the world, yet it does deliver great views to go along with that peaceful, easy feeling. See below for photos of my time a few hundred feet above both Cape May and Beaufort.

Coolest Souviner: Bottles of wine, Hammondsport

Why: Souvenirs don’t have to be useless trinkets, the only requirement in my mind is that they are unique to a certain area. The wine country in and around Hammondsport is known for it’s Rieslings, and it’s what I found I had collected the most of when I opened my trunk at the end of the trip.

Last chance to enter to win a road trip of your own – weekend getaways in the four Coolest Small Towns. Registration closes this weekend with the winner to be announced thereafter.