Solo Train Travel Guide: A Holiday Day Trip to Portland, Maine

by Sojourner

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A day trip to Portland, Maine, is always a good idea! Portland is one of those cities that looks pretty in the winter, fall, and summer. And because of that, you can do tons of seasonal activities on your solo trip to Portland. 

However, this is your itinerary if you are going for an early winter day trip to Portland, Maine.  I went on a solo trip sponsored by Trip Scout for a short weekend that you can do in 24 hours in Portland. After my visit, it is the perfect place to unwind and relax for the holiday season. 

This city may surprise you, from the Christmas trees with lights to eating smokey Maine barbecue and drinking mulled wine! As a solo traveler from the Midwest, I was excited to enjoy this New England city. So here’s your itinerary for a day trip to Portland, Maine. 

FAQs about a solo trip to Portland, Maine

Is Portland good for solo travel?

Overall, a solo trip to Portland is a good option. As a solo female traveler, I felt at ease. The small-town vibe makes it feel cozier, and it’s the perfect place to take a breather and enjoy a slower pace of life. I recommend it for solo female travelers seeking a calming, US domestic vacation. 

How many days do you need in Portland, Maine?

While this blog post focuses on a day trip to Portland, Maine, some folks stay longer. If you want to stay in the city for more than a day, a weekend is sufficient to enjoy the sights and relax. But if you want to visit the surrounding areas, you want to stay longer.

How to travel to Portland, Maine 

All about the Amtrak Downeaster

Romanticize a day trip to Portland, Maine, with a train ride on Amtrak’s Downeaster. This train leaves from Boston’s North Station at various times of the day. The ride takes 2.5 hours and is a great way to skip the traffic, making it a quick and easy option for your solo trip.

Decide on a train class

When you take the Downeaster, you must also pick a train class. The Amtrak Downeaster train ride offers both coach and business class seating. A coach class seat is $29, and a business class seat is $44 one way. With the business class seats, train travelers get a complimentary drink and more legroom. There are fewer seats in business class compared to coach, so solo travelers have more space to walk around and can have a seat to themselves.

How to travel around Portland, Maine

Given its small size, Portland, Maine, is a relatively easy city to travel around. If you want to stay in the city, you can catch an Uber or walk to certain attractions if they are nearby. The Old Port, for example, is a very walkable area to shop and eat. However, rent a car if you want to visit the surrounding areas. 

Where to stay as a solo traveler in Portland, Maine

The Mercury Inn

Though this itinerary could be done in 24 hours, you could stay overnight and take the first train out the next day. No need to rush! So, consider staying at the Mercury Inn for a relaxing and rejuvenating day trip to Portland, Maine.

This inn is perfect for solo travelers who want to be left alone during their trip but have everything they need. The rooms are spacious and comfortable, plus there is a kitchenette you can use. The Mercury Inn tries to be as sustainable as possible in its design, including vintage furniture and eco-friendly amenities such as soap in its suites.

Things to do solo for one day in Portland, Maine

Support local at the Portland Farmers Market

One of the best ways to experience local culture on a day trip to Portland, Maine, is by visiting their local farmers’ market. The Portland Farmers Market is outdoors in the warmer months and indoors during the colder months. You can buy apple cider and enjoy a bagel sandwich next door at Tally’s Kitchen for a breakfast treat. 

Visit the art galleries in the East Bayside neighborhood

If you are a solo traveler who loves to enjoy art, Portland has some options! You can visit the Portland Art Museum in downtown Portland to check out their latest exhibits. However, don’t forget to go to the East Bayside neighborhood to Cove Street Arts. They offer a multimedia collection of pieces for you to learn more about the Portland art community.

Eat lunch at Terlingua

Even though Portland is known for its seafood, it has a delicious barbecue. You can try smokey Maine barbecue at Terlingua, such as wings and sandwiches. And in the colder months, you can add a mug of their mulled wine to your meal.

Taste holiday drinks at Via Vecchia

Via Vecchia is one of the most popular (and cutest) restaurants in the Old Port. On a holiday trip to Portland, you must check out their specials. From a green and red mixed tequila drink to spiked hot chocolate, there is a drink, dish, or dessert that will get you into the holiday spirit.

Get dressed for the Nutcracker at the Maine Ballet

One of the best holiday activities in Portland, Maine, is watching the Nutcracker. The Maine State Ballet puts on a yearly show for locals and tourists to celebrate this iconic production. To make it extra special, get dressed up in the holiday spirit!

Go to the iconic Portland Head Light

A day trip to Portland, Maine, is complete with a visit to the iconic landmark lighthouse. The Portland Head Light is one of the most picturesque places in the city. Right along the water, you can walk the trails or snap photos with one of the most beautiful landscapes in the state. 

Walk around and shop on Exchange Street

On a winter day trip to Portland, Maine, you must hit Exchange Street. Located in Old Port, this street has many local businesses where you can shop and buy holiday gifts. They also make great souvenirs for your trip to remember your solo trip experience.

Enjoy the Pandora Winter Lights

One of the best parts about visiting Portland, Maine, during winter is the holiday decorations. The Pandora Winter Lights is one of those ways to see how Portland gets festive. You can view trees decorated with lights in Congress Square Park, Longfellow Square, Pleasant Street Park and more! And the best part? It’s free!

Three packing essentials for a day trip to Portland, Maine

Comfortable shoes

Whether your day trip to Portland, Maine, is in the summer or winter, you will need comfortable shoes. Many city areas, including restaurants, galleries,  and art museums, are walkable. Also, shoes that don’t hurt your feet will be necessary if you want to enjoy the outdoors.

Layered clothing 

Traveling to Portland in the colder months means the weather can vary. On my solo trip to Portland, I experienced sun, clouds, and a bit of rain. Therefore, wearing layered clothes can help you take them on or off, depending on the temperature. 


No solo trip is complete without your camera! Portland is a very photogenic City, and on your solo trip, you want to capture every cobblestone street, alleyway, and view from the port. I recommend bringing your phone, or even a DSLR or mirrorless camera if you have it, to capture all the memories. 

Why you should visit Portland, Maine

As a solo traveler often on the go, I appreciated my downtime in Portland. It is a city for solo travelers to relax, rest, and recharge. You can embrace being in the moment more than other jampacked solo traveler destinations. I ate more slowly during my meals and lingered a bit longer to enjoy the ambiance of the restaurants I visited. Therefore, a day trip to Portland, Main, is worth the visit!

Will a day trip to Portland, Maine, be your first solo trip? If so, here’s a solo travel planning guide to make it worthwhile.

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