10 Reasons to Visit Portland, Maine During Winter

I had the pleasure of flying back to Portland, Maine to see how the city dresses up for the holidays. If you’re on social media and follow my shares there, you’ll know that I attended the Women In Travel Summit there in May 2019. I participated in so many things that a third-coaster would never get to do during the spring season, that I immediately fell in love with the location and all of the quaint things about it. While in Portland for the week, Visit Portland made sure to pull out all of the stops to ensure that this location is a space that I return to for years to come.

For my week as a Portlander (the first Portland to be exact,) we were dazzled, fed, and regaled to all that Portland and the surrounding cities had to offer. Here’s a bit of what I experienced, and some background information about it all. I’ll hopefully be able to get some more in-depth articles posted to give you all the information you need to know to plan a visit yourself!

Stay at the Inn By the Sea

Inn By the Sea

A few minutes outside of Portland, the Inn by the Sea, located in Cape Elizabeth, is a luxury oceanfront resort that caters to green and sustainable stays and making sure that they respect the entire habitat around the inn while giving people who stay there top-notch service.

While my pockets may not be deep enough to create a luxury travel blog, I do enjoy staying in spaces that give me the FEEL of being in luxury without having to go broke. Inn By the Sea does exactly that. The Inn gives so many vibes of tranquility during the winter season, it’s hard to leave. Between the meals at Sea Glass and the short snowshoeing jaunt to Crescent Beach to watch the waves crash to shore. Which is exactly what I did. The meals are prepared by James Beard trained chef Andrew Chadwick, who is a bit of a celebrity himself with his Lobster Tacos.

The food that we had for breakfast, lunch and dinner each night of our stay was quite luxurious. A lot of thought goes into the menu. Making sure to showcase the things that coastal Maine is known for. Lobster of course, Brussels Sprouts believe it or not, and blueberries. I had my fill of each, and Sea Glass (the on site restaurant) owes me nothing.

Given that these were just appetizers and every single item that I ate at the Inn was delicious, I could bet that this is the best reason to come for a visit. The food alone is worth a flight or a quick train ride up from Boston (the way that I do it when I visit)

While at the Inn by the Sea, I got to do a lot of firsts. First time snowshoeing. First time walking to the beach in the snow, and then being pleasantly surprised that it stopped where the tide came in – science y’all – and the first time sitting on the beach alone in my life. Can you believe it? The beaches are too far from my house in Chicago for me to go during the winter, and well, the water freezes out this way so it all becomes a bit sludgy.

While at the Inn, you can request a complimentary pair of snowshoes for a venture down to Crescent Beach where you can watch the water crash in, and maybe even get to see a lone lobster trap abandoned on the sand.

I had a spa experience with Virginia that relaxed me so much, I could have slept on the massage table. I was able to customize my experience with my essential oil pick and the type of massage that I wanted for a gloriously filled 60 minutes. Before the spa, I could prep in the sauna and even relax MORE in the showers available for spa clients. If you felt that you forgot anything – soap, lotion, feminine hygiene products, razors, and even hair items – they were there for your use.

The Nutcracker

With winter comes all things Christmas, well, for a month or two anyway. It descends over the months of November and December like a blanket of snow, and with it comes The Nutcracker Ballet. The Maine State Ballet puts on the popular ballet for two weekends in November and December, and they make sure to have plenty of Portland representation in the company. It’s also a major draw for families – and even multiple viewings – as was experienced by the little boy behind me who gleefully told his parents everything that would happen next. It made me giggle whenever they would shush him – citing that others may not have seen the ballet before. But c’mon, can you blame a kid for continuing to be enthralled as the Nutcracker slays the mice and rat king?

The Real Portland Tour

If you want to learn all about the city of Portland, Derek Meader is your guy. He was born and raised in Portland and knows the ins and outs of the city to give any tour goer a thorough history of the quaint town. We did the Cape Elizabeth and South Portland Tour where we hit all of the lighthouses along the Portland coast, and were told spots that were great for photo ops. We also learned about the buildings that were around during wars and the many fires that fell on the city causing it to adopt the Phoenix as it’s unofficial mascot. The great fire of 1866 is the one that destroyed most of the city, but since then, more fires came and caused the city to rethink the structure of the city. For example, fire breaks were creatively placed within the city to keep the entire space from burning down again.

While driving through the city, and seeing various cobblestone streets, and colorful doors on the brownstone avenues, we also had a chance to stop and take photos of all of the lighthouses along the coast. Bug Light –

The Porthole

The Porthole is a must visit for anyone who loves lobster. I’ve eaten here twice, and both times I did the lobster special. It allows the person who is hungry to consume two full lobsters for less than $25. You read that right.

We were able to try other things on the menu, but I can’t lie. I was all about the lobster. Caught just in the water a few feet from us, and sweet as sweet could be. Butter sloshed all over it and I was in heaven. You’d be too if lobster is your thing. I attempted to look apologetic at getting two lobsters all for myself, but that attempt didn’t last long.

Head to Freeport, ME

This little town is about a 20 minute drive north of Portland, but worth it for a bit of whimsy, and a photo on the LL Bean Boot. The Flagship store is worth a gander as a destination rather than a place to shop. If you’re wanting to lighten your wallet a little more, the outlets are a great way to spend a day, and make whoever the recipient of your wares a lot happier. The LL Bean Outlet store is definitely worth a visit!

Coastal Maine Botanical Gardens

Have you ever gone walking through a botanical garden at night? Well, you should, especially if you have one close to home base. If you don’t though, the Coastal Maine Botanical Gardens has you covered. We were there in the height of holiday cheer, for an event called Gardens Aglow, but I’m certain you can find the same magic there all year long. As a matter of fact, the urban farmer in me knows you’ll find peace where there’s greenery.

Dinner at Noble Restaurant in Brunswick Hotel

Two things. Tempura fried Shishito Peppers and The Noble Burger. I’m usually not a burger eater when I go to restaurants, but this one came highly recommended by the chef, and I was told by a little birdie that it doesn’t get as much shine as it should – or maybe it does, and people don’t want to admit coming to a coastal town and chowing down on beef.

This baby was nestled between a toasted brioche bun with gruyere, truffle aioli, bacon and tomato and I ate every piece of it.

In The Know Shopping Tour

We were treated to a shopping tour on Saturday morning with In The Know and found out that we were on their vintage/high end shopping tour. While everything that we saw was absolutely gorgeous, most of it was out of my price range, and I would only be able to window shop. What it did accomplish is the ability for me to suggest some great stores to people I know who love that particular line of product, and the great customer service that we received as we entered each store. I will say that my favorite shop was the Rough & Tumble because they make tons of handmade bags and totes that I fell in love with. Specifically the farmers market tote made of waxed canvas. I’m sure that I’ll be ordering one for myself in the near future.

Those shoes up above though? If you’re in the market to being benevolent, I’m a size 7.5 and I really love the navy blue ones on the lower-left corner

Shop at Sea Bags

Right across the alleyway from The Porthole, Sea Bags is a one of a kind custom bag shop that creates wonderful bags from sailcloth. You read that right. They make bags and clutches from the sails used on boats. It’s a great way to recycle and a perfect way to create a product that is unique and a very special gift to give. With the different variants in sails from all over the world, no two bags are the same in placement. These are my types of details for sure!

Maine History Tour

Our group was treated to the Bi-Centennial Tour through Maine Foodie Tours, and I can say from experience it’s an in-depth tour that goes through the rich history of Portland, and the growth from war to present day.

The walking tour begins on Commercial Street and continues through the historic Old Port, downtown and waterfront areas, sharing highlights of Portland’s history since 1632.

Stories and facts are brought to you by trained Portland History Docents (Ph.D.’s as they are called) who will bring history alive on the leisurely stroll.

Some of the locations featured include; the lobster statue, the home of Henry Wadsworth-Longfellow and his place of worship, the Eastern cemetery, the Abyssinian Church, and more.

The tour takes about an hour and a half to two hours depending on questions, and it’s chock full of fun facts. I highly recommend taking both this and a Maine Foodie Tour offered by the same company.

So, when are you booking your ticket? Portland, Maine is a perfect space for those who want small town feel with big city offerings. A wonderful mix of whimsy and charm, and full of history and cuisine to boot.

1 Comment

  • Reply
    Kelly
    January 15, 2020 at 1:27 pm

    I would have loved to have taken that history tour of Portland when we were there a couple years ago. Wish I would have found this post sooner! But we loved Portland and are so excited to go back.

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