Road trip to Maine: There’s a lot more to Maine than Portland and Ogunquit

Portland Head Lighthouse, © week's vacation in Maine: Day One

Here’s a tip: a weekend in Ogunquit is NOT a weekend in Maine. Don’t get me wrong: few vacation spots that cater to the LGBT community match the beauty and accessibility of this self-proclaimed “beautiful place by the sea.” And why not? The food is impressive with Arrow’s (, 41 Berwick Road) topping the list for a special night out that surely could kill your budget. That’s why most will opt for someplace like the equally popular, but decidedly less pricey, Front Porch (, 9 Shore Road). After all, you can move seamlessly from the dinner table to the piano bar upstairs, and then across the street to Maine Street (, 195 Maine Street), which, with a little elbow grease each year, shines up nicely for a full summer of dancing and cabaret. By the time you hit the pillow at Moon Over Maine (, 22 Berwick Road), a favorite B&B for both men and women, you’ve toured the town center and are ready for a day at the beach.

Minus the trilogy of bars and smattering of gay-owned B&Bs, Ogunquit is its beach — and, face it, you can go anywhere on the Cape or scoot down to Newport for that. When people refer to the Maine coast, there is usually a descriptor — most often, “rocky” — and that’s exactly what you find when you head north from Ogunquit for a truly memorable adventure up the coast of Vacationland.

Days Two and Three

Portland’s gay scene? Let’s just say that Maine’s largest city trends onto just about every relevant gay top ten list. Portland is definitely gay, though if your idea of gay is bars and clubs, you’ll be disappointed. People here have either adapted or relented, knowing full well that they can get to Ogunquit in less than an hour for their glitter fix. Of course, everything in Portland is beyond gay friendly. In fact, there doesn’t seem to be a gay/straight distinction, here — case in point is the most recent attempt at instituting a monthly guerilla gay takeover of the city’s “straight” bars. As yet, none of the regulars at the chosen locales have as much as batted an eyelash.

Portland — and Maine — managed to escape the worst of the economic downturn, and the elements that make it a destination are intact: its restaurants, galleries, and bustling Old Port, which rolls down to a stunning harbor of idyllic islands.

Two nights and a couple days in Portland is ample time to take in just about everything it has to offer the gay and lesbian traveler. If you must, there’s the only LGBT nightclub, STYXX (, 3 Spring Street), which tends to reinvent itself every month or so, but always resorts to a formula that attracts the 20-something Long Island Ice Tea set. Blackstones (, 6 Pine Street), a once shadowy leather and Levi bar, is now a typical neighborhood hang-out with pool and the occasional amateur drag show. Our advice? Make reservations for dinner and then hit one of the more catch-all bars for a nightcap and get to bed early so you can spend your day shopping, visiting the Portland Museum of Art (, 7 Congress Street), or hopping on a ferry to picnic and bike on Peaks Island (

Check in to Portland Regency Hotel & Spa (, 20 Milk Street), a former armory in the heart of the Old Port, which has largish rooms in the grand hotel style. That said, it’s not so much grand as it is convenient — you can tip the valet and walk everywhere. For a more personal touch, try the gay-owned Morrill Mansion (, 249 Vaughan Street), a little more out of the way, but, in Portland, that translates to an extra five minutes of walking if you are staying “on peninsula,” in the heart of Portland, which is a must.

Make reservations: Most people come to Portland to eat, and that’s in no small part due to the foodie reputation imposed on the town by the likes of The New York Times and every glossy travel mag worth its salt. If you can get in, try the very delicious but reasonable Caiola’s (, 58 Pine Street, 207-772-1100) in the tony West End. Chef Abby Holmes (formerly of Fore Street) and partner Lisa Vacarro (a former DJ at Zootz) continue to expand on the restaurant, but the food never suffers. The influence here is northern Italian, but the menu tends to be eclectic. If dinner isn’t an option, do brunch.

For more affordable fare, try Norm’s (617 Congress Street). It’s where gay and lesbian Portlanders take a first date, celebrate birthdays, or simply stop in for “a” drink after work only to be pushed out the door five hours later. The pours are generous, and the food is just plain good.

Shop: Believe it or not, Portland’s boutiques for men now rival what’s available for the ladies. Guys, check out Rogue’s Gallery (, 41 Wharf Street) for trendy-cum-traditional picks and creations of local boy Alex Carleton. Portland Dry Goods (, 237 Commercial Street) brings you back to “A Separate Peace,” with its impressive collections that range from Gant Ruggers to the eponymous Portland General Store line of men’s grooming products (fragrances include “tobacco,” “whiskey’” and “professor”). And Joseph’s (, 410 Fore Street) remains one of the only places north of Boston where you can get a pair of Diesel jeans. Fetch (, 195 Commercial St.) is the best place to outfit your pooch. While Eli Phant (, 253 Congress Street) and Angela Adams (, 273 Congress Street) have nice “things” for your home.

Day Four

Take Route 1 — it may get slow in parts, but rarely will you hit an hours-long hold up as you make your way up the coast. The original outlet town, Freeport, is always a draw, but serious shoppers know that the term “outlet” is a misnomer; most retailers these days create a cheap, secondary line rather than ship out their overstock. Freeport does have some highlights, though. The iconic 365/24/7 L.L. Bean (, 95 Main Street) is now a “campus” of stores, including an upscale amusement park featuring a lot of Maine taxidermy and pools of impossibly large trout and salmon (who knew they were that big?). Don’t miss the new L.L. Bean Signature Collection in the flagship store, an edgy update of the tried-and-true togs the retailer is known for. The Home Store stocks a great selection of bedding and furniture with which you can disguise your metro condo as a cottage when the vacation money dries up or the snow starts to fall.

Nearby Wiscasset bills itself as “The Prettiest Village in Maine.” It’s possible. The dozens of colonial and federal style captain’s houses make it certainly worth a stop for architecture buffs. The Musical Wonder House (, 16 High Street), a museum that features 5000+ restored musical boxes, is one-of-a-kind. Rock Paper Scissors (Main Street) is a unique card and home goods shop that places a strong emphasis on finding unusual appointments. And, if you can survive hordes of people and are running ahead of schedule, wait in line at Red’s Eats (Main and Water Streets), a true lobster shack that has been featured on every cable channel and in every coffee table book that feels the need to showcase Maine lobster.

Take a right on Route 27 and spend a night or two in Boothbay Harbor or nearby Southport Island. Because this vacation spot is one of only a handful on Maine’s midcoast that isn’t severed by Route 1, it makes for a more stress-free and adult-oriented destination. Wherever you go, sociability abounds, as does a decent-sized gay and lesbian community ranging from 20-somethings in town for summer work at local music theaters, to year-round same-sex retirees who love the solitude of what is one of the most unpretentious of Maine’s resort towns. You’ll see all kinds mingling at the traditional bars that dot the Boothbay waterfront.

Check in — for upscale digs — at Spruce Point Inn Resort and Spa (, 88 Grandview Avenue), which is a Conde Naste Top 50 All American Getaways destination that offers spectacular views of Boothbay Harbor and unmatched amenities for the area. For those who don’t require such luxury — or can’t afford it — try the Ship Ahoy Motel (, 112 Cape Newagen Road). It boasts the region’s most reasonable rates, and still manages to be right on the water.

Make reservations: The Boothbay area has a decent selection of restaurants, but not much for foodies. 88 at Spruce Point offers its version of haute cuisine. If you are eager to take in the hit-or-miss nightlife of downtown, try Boathouse Bistro Tapas Restaurant and Wine Bar (, 12 By-Way). The menu may be overwhelming, but the food is decent and the bar tends to draw a mixed crowd. If you must have lobster, head east to Robinson’s Wharf and Tug’s Bar (, Route 27, Southport).

Day Five

Boothbay and Southport are a boon for any traveler, with plenty to do for kids, including the Boothbay Railway Village (, 207-633-4727) which offers choo-choo rides and houses a so-so collection of antique autos. Plenty of boat tour companies offer two- and four-hour tours of Boothbay Harbor and the surrounding areas, as well as whale watches and (kid unfriendly) booze cruises. Sans kids, don’t miss the Eastwind Schooner (, 207-633-6598) Sunset Sail hosted by Herb and Doris Smith. By far one of the most relaxing activities in the region, this is an opportunity to pick up a couple bottles of wine, some cheese and crackers and snuggle up with your partner. Don’t forget a sweater; rain jackets are included.

This area is manna for the older gay set: Carousel was filmed on the Boothbay wharf, and old timers still talk about the antics of Shirley Jones and Gordon MacRae. If you hop on Route 27, drive all the way out to the tip of Southport Island public landing, and gaze across channel at Jerry’s Island, you’ll be looking at the home of Margaret Hamilton — yes, the Wicked Witch of the West from The Wizard of Oz. While on Southport, plan some beach time at Hendrick’s Head, where a small swath of beach and a famous lighthouse of the same name provide one of the most picturesque views in the area. Or skip this all — or build in an extra day — to visit Monhegan Island (sidebar).

Days Six and Seven

The drive from Boothbay Harbor to Bar Harbor is one of the prettiest in New England and there are plenty of stops to fill out the day. Each town has its own unique restaurants, shops and things to see: Rockland, Camden, Belfast and Searsport are all worth a walk around. Veer off Route 1 to take in Castine, home to Maine Maritime Academy. Further along, get lost in Big Chicken Barn Antiques and Rare Books ( for some excellent treasure hunting, particularly if you’re into old books and magazines.

Until it was leveled by devastating fires after the turn of the century, Bar Harbor was second only to Newport, Rhode Island as THE playground to the rich (Do the names Astor, Ford, Rockefeller, Morgan and Vanderbilt ring a bell?). And the rich and famous still have homes here, Martha Stewart and John Travolta among them. Although decidedly scaled back, the aura lives on. Larger than any other resort of its type in Maine, activities in Bar Harbor could keep you busy for a week: sea plane tours, kayaks, beaches, plenty of shopping, and great restaurants. But, with only a couple days, you should focus on Acadia, arguably the most beautiful National Park.

Check in: The finer hotels in the Bar Harbor area, including the Asticou Inn (, 15 Peabody Drive, Northeast Harbor), will cost a pretty penny. If you’re okay with budget digs, Anchorage Motel (, 51 Mt. Desert Street) is smack in the center of town. Beware: there are lots of affordable motels nearby, but not within walking distance of the action. If Acadia is your destination, consider camping ( but plan ahead and ask questions.

Make reservations: When in town, Barack Obama prefers Havana (, 318 Main Street), a south of the border favorite well-known for excellent food and drink. If something a little more romantic would be a nice way to wrap up your trip, try Mache Bistro (, 135 Cottage St.) — everything is fresh at this French bistro, the service is impeccable, and jeans are permissible. Believe it or not, Bar Harbor has something that very clearly feels like a full-on gay bar most nights — and the name sorta gives it away— Carmen Verandah (, 119 Main Street). Stop in there for what might be just a game of pool and a decent DJ or, on some nights, a drag performance.

Acadia: The landscape here could not be any more different than Ogunquit, or Portland, for that matter, and that’s why you came. Sweeping postcard views of the ocean, lush forests, ponds, wildlife — everything you’ve heard is true. The only National Park in the country made up of donated private land, Acadia can be enjoyed by car, bike or foot. With limited time, drive the 20 mile Park Loop Road for access to all the major attractions and views. Beyond that, there are some must sees. (1) Cadillac Mountain. This is the highest point on the East Coast; many opt to get to the top early (meaning 4 a.m.) to be able to say that they were among the first in the U.S. to see the sun rise. (2) Jordan Pond. Serenity — when not overrun by tourists. Have a glass of wine and sandwich at the Jordan Pond Restaurant. (3) The cliffs and beaches. There are a multitude, most of them accessible from the Park Loop Road.

Plan your time in Acadia carefully, as there is a lot to see and do — get a good travel book and read it thoroughly.

Day Eight

It has been a long week with a lot of driving. For that reason, head straight for Bangor on Route 95. If the weather is right, play hooky from work and spend another night in Ogunquit. Otherwise, stock up at the New Hampshire Liquor Store and get back to the grind. [x]

Monhegan Island

Monhegan Island is truly getting away from it all. In fact, discovering iPhone service on a recent trip was actually disappointing – you come here to disconnect. After a 12 mile boat ride from Boothbay Harbor, Monhegan has a few general stores in the traditional style, a picture perfect, grand island hotel short on amenities but long on tradition, a number of B&Bs, and enough art galleries to keep you busy for at least a day. Do a day trip to hike the island and take in some spectacular views. Or plan to spend the night, knowing that there is virtually no way to return to the mainland. And don’t expect taxi service once you arrive. There are no cars and no paved roads on the island, and the year round population rarely exceeds 65 people.

Monhegan has long been a retreat for artists and for lovers of art. The Wyeths, William Henry Singer and Edward Hopper have all spent significant time on the island. Their legacy lives on throughout as dozens of would-be and established artists perch along the island’s perimeter each day to capture a landscape that is frozen in time.

It’s best to call ahead for tickets on the Balmy Days Cruises (, Pier 8, Boothbay Harbor) and the fare not only gets you to Monhegan, but almost certainly seal – and more rarely whale – sightings. If you’re staying, check into The Island Inn ( and request an ocean view. After a hike around the island, you’ll be glad you did when you take your wine out to the sloping front lawn and relax in an Adirondack as the sun sets.

A hike, which you’ll want to do regardless of your stay allowance, can range from easy to moderate on the 12 miles of trails. Most choose to walk along the cliffs which are the highest on the Maine coast.

Grab a sandwich for lunch and wine for later at The Novelty, located behind the Monhegan House, which is where you will want to make dinner reservations. The menu is limited, but superb.

Expect to hit the hay early. There are no televisions on site, but plenty of cribbage boards and lots of visitors to the Inn who will more than likely want to share their experience of the day. [x]