Portland Maine Winter Getaway

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Leave the car at home and enjoy a Portland Maine winter getaway on board the Amtrak Downeaster. Portland is a foodie’s dream destination. Enter to win a free trip!

Leave the car at home and enjoy a Portland Maine winter getaway on board the Amtrak Downeaster. Portland is a foodie’s dream destination.

disclosureAs we pulled into the train station in Portland, Maine, I knew this was just what my family needed. With the busy days of school and work colliding with the holiday season, it was the perfect time for a weekend getaway to one of our favorite spots in New England.

My family has loved summertime visits to Portland, so we were excited to experience this vibrant city during the holidays. We took the Amtrak Downeaster train from Massachusetts to Maine. The train experience is the polar opposite of car travel during a holiday weekend. Instead of traffic jams and GPS routes, we were focused on the pretty scenery, comfy seats, and relaxation of the train.

It was great to be able to get up and walk around on the train. The cafe car has several options for snacks and light meals, and the train offers free wi-fi as a nice perk. Time flew by quickly for us during the 2½ hour trip with all the comforts of the Downeaster.

Don't miss the Eastern Promenade if you visit Portland, Maine!

When we arrived in Portland, we fell in love with our hotel before we even saw it. The Westin Portland Harborview has a complimentary shuttle bus that will take you just about anywhere in Portland. The shuttle arrived at the train station just a few minutes after our train pulled in, and the driver, Marty, was very hospitable. We used the shuttle several times during the weekend to get where we wanted to go, so we never missed our car.

Local Food in Portland

Our weekend in Portland revolved around food. Locavore dining is the norm in this city, so we had so many fantastic restaurants and markets to choose from. We focused on places that were easily accessible from our hotel, and we weren’t disappointed once.

Portland, Maine is full of amazing locavore restaurants. Perfect for a foodie vacation!

Congress Squared is the restaurant in the Westin. It’s not your typical hotel restaurant, though. The chef focuses on local ingredients, so the menu changes with the seasons. We had a fantastic dinner here, and the highlights included the cioppino, local redfish, polenta, and bread from Standard Baking Company. The Maine blueberry bread pudding was a fitting ending to the meal.

Duckfat is a Portland institution, featuring delicious fries, sandwiches, and salads. They’re known for long waits for a table, so we got takeout and enjoyed a decadent Duckfat lunch at our hotel. The leafy green salad, fries, and pork panini made on local bread were all delicious.

Maine potato donuts are all the rage in Portland! The Holy Donut is the perfect place to try them.

The Holy Donut is a destination bakery unlike any other. In fact, there was a discussion about donut places in a mom’s Facebook group in my suburban Boston town. People were adamant that the best place to get donuts in the “Boston area” was two hours away from home at the Holy Donut in Portland. After tasting these donuts, I have to agree. These freshly baked donuts get their rich texture from mashed potatoes. They use locally grown potatoes and other high quality ingredients. We’re still craving them now that our trip is over.

The Portland, Maine waterfont is such a peaceful spot to visit.

Rosemont Market has several locations throughout Portland where you can stop in for a high quality sandwich and some fresh fruit. This is a more economical meal than the sit-down restaurants in Portland, and many of their ingredients are locally sourced. We enjoyed sandwiches on their house-made bread while we sat along the waterfront on Sunday.

Local 188 offers a fantastic brunch in Portland, Maine!

Local 188 is a fantastic spot for brunch. The service was exceptional, and we all loved our food. The huevos rancheros helped to fuel me up before our day full of walking. My daughter enjoyed their one-of-a-kind pancake. It’s a cross between a corn muffin and a pancake, cooked in a skillet and featuring special toppings each week. This week it was a peach compote, and the rest of us at the table kept sneaking bites of it. So delicious!

We didn’t have enough time to eat everywhere we wanted, but I have my eye on a couple other restaurants for our next visit. Local Sprouts looks like a great place for breakfast or lunch. And Vinland, which is right next to the Westin, is a uniquely locavore restaurant. Every single item on their menu is sourced in Maine. Vinland would be a wonderful place to splurge for a special occasion meal.

Portland Between Meals

The food is fantastic, but there’s also a lot to do in Portland between meals. We spent our time doing a mix of indoor and outdoor activities that were perfect for the season.

The Westin Portland Harborview is a beautiful, comfortable place to stay in Portland, Maine.

Hotel: The Westin Portland Harborview is a great spot for a weekend getaway. Located on the west side of town in the Arts District, the hotel is within walking distance of just about anywhere you’d want to go in Portland. The rooms are spacious and the beds are very comfortable. The free shuttle bus is such a convenient perk. The shuttle driver even waited for my husband outside Duckfat while he picked up our takeout order. Amazing customer service!

Nature: Even with a chill in the air, we were able to take in the waterfront beauty of Portland as we walked along the Eastern Promenade. The views of the bay were breathtaking, and we were happy to walk off all the food mentioned above. 🙂

There are so many fun shops in Portland, Maine! Perfect for a holiday shopping trip.

Shopping: There are so many independent shops throughout Portland. We spent time in Old Port and the West End on Small Business Saturday, meandering through bookstores, gift shops, and an art store. There were lots of unique gifts in these shops, so we got a start on our holiday shopping.

Museums: The Portland Museum of Art is just down the street from the Westin. This is the #1 rated attraction in Portland on TripAdvisor, and we were impressed by the art collection here. This family-friendly museum is going through a transformation to help all ages interact with its collections. After a brief closure in January, the museum will re-open with a new colorful animal collection and a multigenerational, participatory space, among other changes. I look forward to visiting the museum again after its transformation.

The Children’s Museum and Theatre of Maine is located right next door to the Portland Museum of Art. My children are a bit too old for this museum, but I’ve heard great things about it. The museum and theater sound like a perfect place to visit during the winter with younger kids.

Horse and carriage rides are a free holiday activity to enjoy during December in Portland, Maine.

Holiday Events: Horse and carriage rides are available for free during the weekends of December. This was such a relaxing way to see the city all dressed up for the season. It got us in the holiday spirit!

Disclosure: My family was hosted by the Amtrak Downeaster, the Westin Portland Harborview, Congress Squared, and the Portland Museum of Art. All opinions are my own.


  1. We went to Portland once many years ago for a weekend. I’d love to head back and explore it some more!

  2. Ok, so I tried to comment via the entry-form-not sure if it worked. Love all the ideas of things to do and places to eat!! If I win 🙂 I’ll be sure to follow your suggestions.

  3. I have not been able to afford a vacation in years which is unfortunate because traveling is my PASSION, so this would be a wonderful treat! I have never been to Maine but have always wanted to visit. I love exploring, hiking, and eating so this would be an amazing vacation!

  4. How fun! I went to grad school in Boston and loved visiting Maine (only one time though). I am entering but not sure if there is a expiration date for taking advantage of this trip. Anyway, I would definitely go grab some donuts- drooling!

  5. I absolutely love Maine. We were just there in October to visit friends and can not wait to go back. Portland is one of my favorite places every time we visit!

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