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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. 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.
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.
The influence here is northern Italian, but the menu tends to be eclectic. For more affordable fare, try Norm’s (617 Congress Street).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 dozens of colonial and federal style captain’s houses make it certainly worth a stop for architecture buffs.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. The Musical Wonder House ( 16 High Street), a museum that features 5000 restored musical boxes, is one-of-a-kind.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.