Imagine sipping champagne in a flapper dress while jazz wafts through the air.

No time machine needed – Maine’s got you covered with these Roaring Twenties-esque spots!

1. Victoria Mansion (Portland)

Step into this opulent Italian villa-style mansion, and you’ll half expect Jay Gatsby himself to greet you at the door.

Built in the 1860s, Victoria Mansion is a jaw-dropping example of pre-Civil War opulence that would make even the most jaded socialite swoon.

With its brownstone exterior and lavish interiors, it’s like someone took a slice of Newport and plopped it right in the heart of Portland.

Inside, it’s a feast for the eyes that’ll make you wonder if you’ve accidentally stumbled onto a movie set.

The ornate plasterwork, trompe l’oeil walls, and Turkish smoking room are so over-the-top, you might need sunglasses just to look at them.

And don’t get me started on the flying staircase – it’s so dramatic, it probably has its own agent.

2. The Strand Theatre (Rockland)

If you’ve ever wanted to feel like a 1920s movie star, sashay your way into The Strand Theatre in Rockland.

This art deco gem has been dazzling audiences since 1923, and let me tell you, it’s aged better than most of us.

The marquee alone is enough to make you feel like you’re about to attend the premiere of “The Jazz Singer.”

Inside, the vintage charm is cranked up to eleven.

The plush red seats and ornate ceiling will have you half-expecting a cigarette girl to come by selling Lucky Strikes.

And while the movies might be in color and sound these days, the atmosphere is pure Roaring Twenties.

Just try not to get too carried away and start doing the Charleston in the aisles.

3. The Colony Hotel (Kennebunkport)

Perched majestically on a bluff overlooking the Atlantic, The Colony Hotel in Kennebunkport is what happens when coastal Maine decides to put on its fancy pants.

This grand dame of hotels has been turning heads since 1914, and it’s not hard to see why.

With its brilliant white exterior and emerald green shutters, it’s like a giant, glamorous wedding cake by the sea.

The sprawling porch, complete with rocking chairs, is the perfect spot to sip a gin rickey and pretend you’re waiting for your polo-playing beau to return from the Hamptons.

And the saltwater pool?

It’s so fabulous, you half expect Esther Williams to emerge doing a synchronized swimming routine.

Just remember, old sport, the hotel is seasonal – so plan your Jazz Age fantasy accordingly.

4. Norumbega Inn (Camden)

If Gatsby decided to ditch West Egg for the rugged coast of Maine, he’d probably end up at the Norumbega Inn in Camden.

This stone castle (yes, you read that right) looks like it was plucked straight out of a fairy tale and plonked down on the Maine coastline.

It’s the kind of place where you’d expect to find a flapper princess locked away in the tower, waiting for her bootlegger prince to rescue her.

Built in 1886, this architectural stunner combines the grandeur of a European castle with the charm of a New England B&B.

The turrets and gables are so picturesque, they make other buildings look like they’re not even trying.

And the views of Penobscot Bay?

Let’s just say they’re the kind that make you want to write overwrought poetry about the sea and your lost love.

5. Portland Observatory (Portland)

Want to feel like you’re on top of the world (or at least Portland) in true Gatsby style? Climb to the top of the Portland Observatory.

This octagonal tower, built in 1807, is the only remaining historic maritime signal tower in the United States.

It’s like a lighthouse, but with more swagger.

As you ascend the 103 steps, imagine you’re climbing to your private speakeasy in the sky.

The panoramic views of Casco Bay and the city below are so spectacular, you’ll feel like the king (or queen) of Portland.

Just don’t get any ideas about signaling to passing ships about any illicit liquor deliveries, okay?

6. Bar Harbor Inn (Bar Harbor)

The Bar Harbor Inn is the kind of place that makes you want to pack a steamer trunk full of linen suits and flowing dresses, even if you’re just staying for the weekend.

Perched on Frenchman Bay, this grand hotel has been the playground of the rich and famous since the Gilded Age.

It’s so fancy, even the seagulls probably wear monocles.

The expansive lawn, dotted with Adirondack chairs, is perfect for a game of croquet or for dramatically fainting after receiving shocking news about your secret lover.

And the wraparound porch?

It’s practically begging for you to stand there, cocktail in hand, gazing wistfully out to sea while contemplating the fleeting nature of youth and beauty.

Just try not to get too carried away with the role-playing, old sport.

7. Poland Spring Resort (Poland)

Poland Spring Resort is what happens when Mother Nature decides to throw a Gatsby-style bash.

This sprawling resort, with its pristine golf courses and mineral springs, has been a hotspot for the well-heeled since the 1800s.

Related: This Roaring Ocean Spectacle in Maine Will Leave You in Awe

Related: You’ll Think You’re in the Enchanted Forest at this Hidden Hiking Trail in Maine

Related: This Heartwarming Hiking Trail in Maine Will Remind You of Lassie Come Home

It’s the kind of place where you’d expect to see flappers doing the foxtrot on the lawn while butlers serve cucumber sandwiches.

The historic Maine State Building, moved here from the Chicago World’s Fair of 1893, adds an extra layer of grandeur.

It’s like someone decided to sprinkle a bit of world’s fair magic onto an already fabulous resort.

And let’s not forget the legendary Poland Spring water – it’s so pure, it probably turns into champagne if you’re fancy enough.

8. Eastland Park Hotel (Portland)

The Eastland Park Hotel in Portland is like the Great Gatsby of hotels – it’s got stories, it’s got style, and it’s definitely seen its fair share of wild parties.

This grand dame of Portland has been turning heads since 1927, and honey, she’s still got it.

The brick exterior is so handsome, it probably makes other buildings feel insecure.

Inside, it’s a glorious mix of old-world charm and modern luxury.

The lobby is the kind of place where you’d expect to see flappers and philosophers engaged in witty banter.

And the rooftop bar?

Let’s just say the views of Portland are so spectacular, they could make even the most jaded socialite gasp.

Just remember to bring your best Gatsby-esque one-liners – you’ll need them to fit in with this crowd.

9. Ogunquit Playhouse (Ogunquit)

If you’ve ever wanted to feel like a 1920s Broadway star (without the grueling rehearsals and tap dance injuries), the Ogunquit Playhouse is your ticket to showbiz glamour.

This historic theater has been dazzling audiences since 1933, and it’s still got more sparkle than a flapper’s headband.

The colonial revival-style building is so charming, it could probably get a standing ovation just for existing.

Inside, it’s all vintage elegance and theatrical magic.

The red velvet seats are so plush, you’ll feel like royalty even if you’re in the nosebleed section.

And who knows?

You might just catch the next big thing before they hit the Great White Way.

Just try to resist the urge to jump on stage and belt out “Puttin’ on the Ritz” – leave that to the professionals, darling.

10. The Abbe Museum (Bar Harbor)

Now, I know what you’re thinking – how can a museum dedicated to Maine’s Native people make me feel like I’m in The Great Gatsby?

Well, hold onto your cloche hats, because the Abbe Museum in Bar Harbor is housed in a building so stylish, it could make Jay Gatsby jealous.

The downtown location, with its sleek design and modern exhibits, is a far cry from the stuffy museums of yore.

It’s the kind of place where you can imagine chic flappers and dapper gents discussing indigenous art over martinis.

The blend of important cultural history and architectural elegance is so seamless, you’ll feel both enlightened and glamorous.

Just remember, no Charleston dancing near the artifacts, please.

11. Bowdoin College Museum of Art (Brunswick)

If Gatsby had gone to college (and let’s face it, he probably claimed he did), he would have felt right at home at the Bowdoin College Museum of Art.

This neoclassical beauty is so grand, it makes other campus buildings look like they’re wearing sweatpants to a black-tie affair.

Inside, it’s a treasure trove of art that would make even the most jaded Upper East Sider swoon.

From ancient artifacts to contemporary masterpieces, it’s got more culture than a year’s supply of yogurt.

And the best part?

You can soak up all this sophistication without having to sit through a single lecture.

Now that’s what I call higher education!

12. Merrill Auditorium (Portland)

Merrill Auditorium in Portland is the kind of place that makes you want to dust off your opera glasses and practice your most sophisticated “Bravo!”

It’s so elegant, even the pigeons outside probably wear tuxedos.

This grand performance space, with its art deco touches and stellar acoustics, is where Portland goes to get its culture on.

Whether it’s hosting the symphony, Broadway shows, or world-class musicians, Merrill Auditorium brings a touch of metropolitan glamour to Maine’s largest city.

It’s like someone took a slice of Carnegie Hall and plopped it down in Portland.

Just try not to get too carried away and start conducting from your seat – leave that to the professionals, old sport.

13. Portland Museum of Art (Portland)

Last but certainly not least, we have the Portland Museum of Art – a place so stylish, it makes other museums look like they’re wearing last season’s exhibitions.

Housed in a beautiful brick building that screams “I have important things inside,” this museum is the cultural equivalent of a really good hair day.

With its impressive collection spanning from the 18th century to contemporary works, it’s like a time machine for art lovers.

You can go from admiring colonial portraits to scratching your head at modern installations faster than you can say “abstract expressionism.”

And the best part?

You can pretend to understand everything while sipping wine at one of their evening events.

Now that’s what I call cultured!

So there you have it, folks – 13 spots in Maine that’ll make you feel like you’ve stepped into the pages of Fitzgerald’s masterpiece.

Now, where did I put my dancing shoes?