Ever wondered what it would be like to journey back to the extravagant era of the Roaring 20s?
This road trip through Maine will uncover 13 sparkling hidden gems that echo the glamour and charm of the Jazz Age.
1. The Strand Theatre (Rockland)
Picture this: You’re strolling down Main Street in Rockland, when suddenly, a dazzling neon sign catches your eye.
That’s right, folks – it’s the Strand Theatre, a cinematic gem that’s been lighting up the night since 1923.
This isn’t just any old movie house; it’s a bona fide time capsule of entertainment history.
Step inside, and you’ll feel like you’ve wandered onto the set of a classic Hollywood film.
The art deco details will have you swooning faster than a silent film starlet.
But don’t worry, the movies here are far from silent these days.
From indie flicks to blockbusters, the Strand serves up a smorgasbord of cinematic delights that would make even Charlie Chaplin trade in his bowler hat for some popcorn.
2. Victoria Mansion (Portland)
Hold onto your monocles, because we’re about to dive into the lap of luxury at Victoria Mansion in Portland.
This architectural marvel might predate the Roaring Twenties, but it’s got enough opulence to make any flapper swoon.
Built in the 1860s, this brownstone beauty is like the great-grandaddy of 1920s extravagance.
With its ornate interiors and enough gold leaf to make Midas blush, it’s a glimpse into the kind of swanky pad Gatsby might have envied.
Just don’t get any ideas about throwing a wild party here – the antique furniture probably can’t handle your Charleston moves.
3. The Colony Hotel (Kennebunkport)
Ahoy, socialites! Our next stop is The Colony Hotel in Kennebunkport, where seaside glamour meets 1920s charm.
Perched majestically on a bluff overlooking the Atlantic, this grand dame of hotels has been hosting the well-heeled since 1914.
With its brilliant white facade and emerald lawns, The Colony looks like it’s been plucked straight from a vintage postcard.
Inside, you’ll find a delightful mix of old-world charm and modern comforts.
Just imagine sipping a gin rickey on the veranda, watching the waves crash below.
It’s enough to make you want to trade in your car for a steamship and your smartphone for a telegram.
4. Norumbega Inn (Camden)
Hold onto your hats, folks, because we’re about to enter a real-life fairy tale.
The Norumbega Inn in Camden isn’t just a bed and breakfast – it’s a stone castle that looks like it’s been teleported straight from a storybook into coastal Maine.
Built in 1886, this turreted wonder predates the Roaring Twenties, but it’s got enough Gilded Age glamour to make any Jazz Age junkie weak at the knees.
With its intricate stonework and commanding presence, it’s the kind of place where you half expect to see Jay Gatsby himself strolling across the lawn, champagne flute in hand.
5. Portland Observatory (Portland)
Alright, high rollers, it’s time to elevate our perspective – literally.
The Portland Observatory might not scream “Roaring Twenties” at first glance, but hear me out.
This octagonal tower, built in 1807, offers a bird’s-eye view of Portland that would make any 1920s tycoon green with envy.
Imagine being a big shot in the 20s, using this tower to spot your steamship coming into port, laden with your latest shipment of… er, “totally legal imports.”
Wink wink, nudge nudge.
Today, you can climb to the top for a panoramic view that’ll knock your spats off.
Just be prepared for a workout – those 103 steps are no joke!
6. Bar Harbor Inn (Bar Harbor)
Darlings, pack your finest bathing costumes because we’re off to the Bar Harbor Inn.
This seaside stunner has been the crown jewel of Mount Desert Island since the 1800s, but it really hit its stride in the Roaring Twenties.
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Picture this: you’re lounging on the sprawling lawn, martini in hand, watching the yachts of the rich and famous bobbing in Frenchman Bay.
The air is filled with the sound of clinking glasses and jazz drifting from the veranda.
It’s the kind of place where you might bump into a Rockefeller or a Vanderbilt – or at least pretend you have after a few too many gin fizzes.
7. Poland Spring Resort (Poland)
Hold onto your golf clubs, because we’re teeing off at the Poland Spring Resort.
This sprawling complex has been a playground for the well-to-do since the 1790s, but it really hit its stride in the Roaring Twenties.
With its pristine golf course (one of the oldest in New England) and its famed natural spring water, Poland Spring was the place to see and be seen.
Today, you can still channel your inner 1920s golf pro on the links, or take a swig of that famous spring water.
Who knows? It might be the secret to eternal youth – or at least to curing your Prohibition-era hangover.
8. Eastland Park Hotel (Portland)
Alright, high rollers, time to check into the Eastland Park Hotel in Portland.
This towering brick beauty opened its doors in 1927, just in time to become the hottest spot in town during the tail end of the Roaring Twenties.
With its imposing facade and prime location, the Eastland was where the who’s who of Portland came to see and be seen.
Today, it’s been revamped and renamed, but you can still soak in those Jazz Age vibes.
Just don’t try to sneak any bathtub gin into your room – those days are long gone!
9. Ogunquit Playhouse (Ogunquit)
Ladies and gents, it’s showtime at the Ogunquit Playhouse!
This theatrical gem has been dazzling audiences since 1933, making it a youngster compared to some of our other stops.
But don’t let that fool you – it’s got enough razzle-dazzle to transport you straight back to the heyday of vaudeville.
From Broadway hits to star-studded performances, the Ogunquit Playhouse has seen it all.
Just imagine the ghosts of flappers past, sneaking in a flask of hooch to enjoy during the show.
Today, you can catch a performance without the need for secret passwords or hidden speakeasies – but where’s the fun in that?
10. The Abbe Museum (Bar Harbor)
Now, let’s take a moment to appreciate some history that goes way, way back before the Roaring Twenties.
The Abbe Museum in Bar Harbor is dedicated to the Wabanaki Nations, the indigenous peoples of Maine, and the Maritimes.
Founded in 1926 (hey, there’s our 20s connection!), the Abbe Museum offers a fascinating glimpse into a culture that was here long before jazz and flappers came along.
It’s a sobering reminder that while we’re having fun with our 1920s nostalgia, there’s a much deeper history to explore in Maine.
11. Bowdoin College Museum of Art (Brunswick)
Art lovers, rejoice! We’re making a stop at the Bowdoin College Museum of Art.
While the museum itself dates back to 1894, its collection includes some stunning pieces from the 1920s and beyond.
Housed in a building that looks like it could have been plucked from ancient Greece, this museum is a delightful mishmash of old and new.
From ancient artifacts to modern masterpieces, it’s got something for every art aficionado.
Who knows?
You might even discover your inner Picasso – just don’t try to sell your doodles as lost masterpieces, okay?
12. Merrill Auditorium (Portland)
Music lovers, tune your ears!
We’re stopping by Merrill Auditorium in Portland.
While this grand performance space didn’t open until 1997, it occupies a building that dates back to 1912 and has seen its fair share of Roaring Twenties revelry.
Today, you can catch everything from classical concerts to Broadway shows in this acoustically perfect hall.
Just imagine the ghosts of flappers past, tapping their toes to the rhythm.
And hey, if you hear some unexplained jazz coming from an empty corner, don’t worry – it’s probably just the spirit of the Roaring Twenties living on!
13. Portland Museum of Art (Portland)
Last but certainly not least, we’re wrapping up our tour at the Portland Museum of Art.
While the museum’s current building is a modern marvel, it houses a collection that spans centuries, including some fabulous pieces from the 1920s.
From Winslow Homer to Marsden Hartley, the museum showcases the best of Maine’s artistic legacy.
And let’s not forget the architecture – the museum’s campus includes the McLellan House, a Federal-style mansion that dates back to 1801.
It’s like a time machine in building form!
So there you have it, folks – a whirlwind tour of Maine’s most dazzling 1920s-inspired gems.
From swanky hotels to artsy hangouts, we’ve Charleston-ed our way through the best the Pine Tree State has to offer.
Let the journey unfold!
This map is your guide to every twist, turn, and unforgettable stop ahead.
Now, if you’ll excuse me, I need to go practice my fox-trot and mix up a batch of bathtub gin.
Just kidding about that last part… maybe.