Free Mini Guide: Winter Weekend in Portland, ME

Free Mini Guide: Winter Weekend in Portland, ME

3 day itinerary for a winter weekend in Portland, ME. Portland is known for a summer hotspot - BUT the real secret is that it's the perfect cozy winter getaway. You will beat all the crowds that the warm months bring!
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Lodging

The Press Hotel, Autograph Collection
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Canopy by Hilton Portland Waterfront
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Day 1 

Lunch & Brews at Allagash Brewery

Allagash Brewing Company
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Bite into Maine
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One of the best Escape Room's in New England - I recommend "Escape your Fears" or "Southport's School for Wizard's"

Maine Escape Games
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Apres Happy Hour at Hunt & Alpine 

The Portland Hunt & Alpine Club
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Dinner at Black Cow - Portland's Best Burger - Be Sure to order Table Fries!

Black Cow Burgers & Fries
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*If you are feeling more of a fancy vibe then I suggest David's for a classic Portland Dinner

David's Restaurant
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If you have the energy - End the night at Blyth & Burrows. I challenge you to find the secret bar room (hint: never judge a book by it's cover).

Blyth & Burrows
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Day 2

Start your day right with breakfast at Dutch's. Always order a pastry - I suggest their donuts

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Take a scroll along the Eastern Prom. Even in the Winter the Eastern Prom walk is a great way to take in Portland's waterfront while burning some of those calories.

Eastern Promenade
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Warm up and enjoy the cozy vibes of Apres cider house.

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Grab some grub at the Duckfat Frite Shack. I believe their most unrated menu item is their Coffee Frappe. It is worth it even in the cold weather - trust me!

Duckfat Frites Shack
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Stop by the Distillery for a tasting.

Hardshore Distilling Company
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Dine at Portland's Hottest restaurant Twelve. I recommend booking the chef's counter and ordering the tasting menu with the addition of the lobster roll. If tasting menus aren't your thing grab a seat at the bar and order a la carte. 

Twelve
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Insider tip - reserve a chef's counter seat!
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Enjoy a nightcap at MAPS bar located below the cobblestones. 

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Day 3

No Portland trip is complete without feasting at Bayside American Cafe. I will warn you this is a hot spot and most likely you will  have to wait for a table. BUT it is worth the wait for the cinnamon roll pancakes!

Bayside American Cafe
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If you want a lighter option stop by Bard Coffee for your caffeine fix and then run across the street to Gross Confections for a delicious pastry

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Gross Confection Bar
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Shop in the old port at some classic Maine stores.

Lisa-Marie's Made in Maine
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Maxwell's Pottery Outlet
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End your Maine adventure for a Lobster and a view at Luke's.

Luke's Lobster Portland Pier
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* * *
ABOUT THE AUTHOR
Founder of The Prepped Traveler. Lover of unique boutique hotels that won't break the bank and food stops that will fill your soul. Expert in New England travel itineraries that include adventure and good food! Born and raised New Englander, based in Massachusetts
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