Rustic charm, great food, gay-friendly destinations, and postcard-perfect fall leaves make this winding trip the perfect autumn giveaway
By James Parker Sheffield

Maine wasn’t originally on my list of must-visit gay getaways. When a work trip promised me Portland in October, my initial response was, “Oh, that Portland.” Fortunately, it turns out Maine is one of the most LGBT-friendly destinations on the map, and beyond picturesque in fall.

Maine offers a unique rocky coastline, world-renowned parks, quaint storefronts, and fantastic locally sourced food. The spectacular fall foliage peaks around mid-October, and Maine is a premier location to enjoy the colors. If you’re itching for a new adventure, or just need Mother Nature’s Xanax during a tumultuous election year, Maine is just what the doctor ordered.

You can get a well-rounded view of the foliage and waterways with just three-to-four days at your disposal. Delta offers daily, nonstop flights to Portland, and car rental agencies are available at its small airport. You’ll want to drive to make the most of your time and the scenery.

Now all you need is a route. That’s what this Portland – Bar Harbor – Rockland – Portland itinerary is all about. Thank us later.

Portland is Maine’s most populated city. It also features the state’s largest Pride celebration, held each year over the third weekend in June. With vast offerings for tourists, you can do anything from kayaking excursions to shopping to ghost and vampire tours.

For craft beer enthusiasts, Portland is home to more than a dozen local breweries. As a specialty for the fall, Shipyard offers perfectly spiced pumpkin ale on tap that’s not to be missed. The gay nightlife scene includes Styxx and Blackstone’s, which is as close to a leather bar as you can get while standing in a Norman Rockwell painting.

If you’re looking to outfit yourself appropriately – and who isn’t? – the L. L. Bean flagship store is 20 minutes from Portland’s city center. Stock up on life-lasting flannel-lined khakis, cableknits and outerwear.

When you’re ready, hit the road for a three-hour drive north on I-95. You might be tempted to take Route 1, but don’t! It would double your drive time to Bar Harbor.

Once there, the jaw-dropping natural wonders include Mount Desert Island and Acadia National Park. There’s no shortage of hiking, biking or rock climbing in the area, and the views are breathtaking. If you prefer a bit of structure, tours are offered via bus, boat and plane, and if you’re after a special experience with nature, whale-watching trips and lobster boat excursions are available daily.

In addition to the parks in the area, Bar Harbor offers great waterfront shopping and dining. Cruise ships and other large vessels regularly port here, so you might even get lucky and meet an attractive sailor or two.

After getting your fill, head south to Rockland via Route 1. This two-hour drive travels along a gorgeous rocky coastline. Once there, Rockland offers ample options for exploration of the area’s natural surroundings and history.

By this point, if you haven’t been on a boat, it’s time. There are few things to make you feel more grown up or important than hanging out on a sailboat in New England. Rockland is known for its amazing sunrises, but if you miss that in favor of an evening sail featuring champagne and Maine lobster, like Captain Jack’s Lobster Boat, absolutely no one will blame you.

Be sure to check out the Maine Lighthouse Museum and the Maine Center for Contemporary Art. “Interesting” souvenirs include the gift shops’ gummy lighthouse candies. Funny thing about those: they don’t look like lighthouses. I won’t ruin the surprise, but trust me, your gays will love them.

Route 1 reconnects to the interstate, and the drive back to Portland is about an hour and a half. Make the trip next month, and you’ll hit the airport relaxed, well fed, and ready to deal with the realities of Election Day.