Forget Portland! Visit Maine’s Oldest City With Secret Islands
As Portland has become a trendy hotspot in recent years, the rest of Maine is essentially the last frontier of the East Coast.
Maine tourists don’t typically venture beyond Portland, with the exception of Acadia, one of America’s prettiest National Parks.
But there’s so much more to explore away from the charismatic brick roads winding through the Old Port, ample blue-water beaches, and endless lobster vendors of Portland.
Maine’s small towns are truly delightful, and one of the best is often overlooked, even though many roadtrippers pass through on the way to Portland.
Just across the New Hampshire-Maine border lies the state’s oldest city, dating back to the 1600s, over a century before America was, well, America and the Gulf of Mexico was still…
Ahh, never mind.
Not only is this hidden gem still exuding the charm of a bygone era, standing the test of time, but it beholds numerous secret islands and a treasure trove of maritime history and coastal charm waiting to be (re)discovered.
Welcome To Kittery, Maine: The East Coast’s Best Kept Secret
Ever heard of Kittery? Unless you’re from the region, likely, you haven’t. With Portland hogging Maine’s travel scene, it’s completely understandable.
But Kittery has existed for hundreds of years, and gatekeepers have done a phenomenal job of remaining tight-lipped about one of the East Coast’s best-kept secrets.
Being a town of only 10,000 residents, there’s no commercial airport here, but there is in neighboring Portsmouth, New Hampshire, another charming coastal town in its own right with connecting flights from budget airlines, Breeze and Allegiant, from popular hubs such as Orlando (MCO).
Otherwise, Boston International Airport (BOS) is only an hour away and has a lot more options.
Kittery has a fascinating timeline spanning centuries from formerly being named Amiciskeag by Native Americans years before tribes engaged in armed conflicts with French and English settlers for rights to the land, and we all know how that ultimately turned out…
Furthermore, what may seem like a tall tale is actually true. Pirates (yes, real-life pirates!) like infamous Blackbeard, once traversed Kittery’s isles, so you may want to bring a metal detector along as there have long been rumors of lost treasure left behind.
As Kittery stands today, you can’t help but notice the aesthetics of seafarer charm and the palpable sense of history throughout town, with sites like Fort McClary, a military fort used as far back as the Revolutionary War.
But even with all the historical significance, don’t expect Kittery to be a boring glimpse into the past.
Downtown (a.k.a. Kittery Foreside) has been transformed with quirky artisan shops, upscale cafes serving craft coffee concoctions, and a surging food scene leaving one travel guide to essentially describe Kittery as a mini Brooklyn.
Kittery’s Secret Islands: Barbecue, Beaches, And Waterfront Stays
Some islands of Kittery’s scenic shorelines are off-limits for tourism hence the secret. The good news is there’s plenty of islands nobody ever seems to talk about that make for awesome spring and summer getaways.
Let’s start with Gerrish Island. Visit Fort Foster Park for only $25, another historical site, but this one boasts small tranquil beaches and sweeping coastal scenery, including quintessential lighthouses.
Your best bet for the full Gerrish Island experience is to book a vacation rental on Vrbo or Airbnb since public access is closed (except for Fort Foster).
Next up is the Isle of Shoals, a series of islands spanning across state lines but featuring fun-to-say Smuttynose Island and Appledore Island on the Maine side of the dividing line.
To get here, though, you’ll need to cross over to Portsmouth and hob aboard a boat from Isle of Shoals Steamboat Company.
Unfortunately, they leave us hanging with the dreaded “coming soon” message on their calendar, but as the weather gets warmer, it’s all but certain they’ll restart service sooner rather than later.
Here is where I said you might want to bring a metal detector ,as these are pirates’ old stomping grounds,
Circling back toward town, there’s a pair of islands worth visiting: Badger Island (Maine) and New Castle (New Hampshire).
Badger is connected by bridge, so you can drive here, and boasts great eats like local favorite Ore Nell’s Barbecue served ‘Central Texas style’, while New Castle offers a great selection of waterfront hotels like Wentworth by the Sea with rave reviews claiming it’s a ‘charming historic hotel with a water view’ and has ‘lovely clean rooms antique style’.
Cheaper Than Portland
Maybe I’m in an exclusive club, but when I visited Portland, I was sticker-shocked by hotel prices. In fact, it’s the only city I’ve chosen to stay in a Motel 6 to save money.
Worst of all, they didn’t leave the light on for me! What a sham!
Portland has become so trendy, there’s no way I’m the only one noticing the city’s high prices whether it be top-rated lobster rolls or hotel rooms.
Travelers don’t have to worry about that in Kittery. In fact, one of its claims to fame, besides being Maine’s oldest city, is its shopping.
East Coast residents from all over make day trips to shop ’til they drop at the Kittery Outlets. Affordable prices don’t stop there, though.
Stay at the revamped Kittery Inn & Suites for just $64 this spring or The Water Street Inn, holding a perfect 5.0 Google rating, for $128.
Last but not least, it’s a must to have lobster, right? Dave’s Maine Cafe has lobster rolls for just $18!
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This article originally appeared on TravelOffPath.com
Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.