What to Do in Portland, Maine in 8 Hours!

7:00 AM // What to do in Portland, Maine in 8 hours
I got this beautiful postcard from an oil painter who is posted up right next to the Portland Head lighthouse with various prints of his art. I loved this one!

It's July which means that we only have a mere three weekends left to enjoy this city. Since both Joe and I work during the week, we knew that we really had to use our time on the weekends wisely. Our last two weekends in July are filled with wedding-related activities so in reality, we only had two weekends left to enjoy Boston. Just thinking about it makes me want to cry! How did the time go by so quickly?!

This is why Joe and I decided to take a very spontaneous trip to Portland, Maine last weekend. We literally didn't have anything planned and just kind of planned things on the go like finding public transportation (since we don't have our car), finding things to do, etc. // What to do in Portland, Maine in 8 hours . // What to do in Portland, Maine in 8 hours

Joe would have been so against the idea of taking a spontaneous trip about three years ago but I tend to be a very spontaneous person so I think he's started to get used to my spontaneous requests. The both of us knew that we wanted to go to Maine so he actually got right on board with me. 

Friday Night: I quickly googled a way for us to get to Portland, Maine and we decided to take the train! It was going to be a 2.5-hour ride for us from Boston. This was perfect because we could use our time on the train to look up things to do while in Portland! 

Getting from Boston to Portland, Maine via Train: You'll want to take the train from North Station. Tickets are $29 per person one-way (we purchased ours on a Saturday). There are some wide gaps in the times that the train leaves so I would plan in advance to board a train in time to make it into Portland, Maine at a decent time. 

Transportation once in Portland, Maine: With our itinerary, we definitely had to take advantage of lyft. We didn't really know how to work the buses in Portland and the sights we wanted to see weren't exactly walking distance! 

Saturday: We slept in a bit because we had been entertaining my brother and friend that week so we recovered from that a bit and then went on our merry way to Portland, Maine! I didn't quite line up the time for getting on the train very well and we ended up having to wait at the train station until 4:15 PM to even start the 2.5-hour ride. This meant that we'd get into Portland after 7 PM and really only have time to grab dinner and not much else. 

Realizing this, we decided to book a hotel room in Portland, Maine on the fly. This is not the first time that we've done this so I was actually quite ready for a mediocre hotel experience (haha!). There weren't any airbnbs available because of how soon we were trying to book a room. (The lesson here is to plan trips in advance, but spontaneous trips can still happen). We didn't have any of our toiletries, no change of clothes, etc!!! I hate myself for even admitting publicly that this happened but seriously, this was the most spontaneous of spontaneous trips. 

Things to do in Portland, Maine in 8 Hours

Take advantage of the time that you have to check out the amazing food scene in Portland, Maine and try getting different courses at different restaurants! We decided to do an appetizer, entree, and drinks at three different locations and it was so fun! If you are there on a weekend you will have waits from 1 hour - 1.5 hours (for even just a party of two) so I would recommend preparing yourself to be ready to do lots of waiting. 

1) APPETIZER: Get fries at DuckFat

They fry their fries in duck fat so of course it's automatically amazing. The fries come with some unique sauces, we got the curry mayo and the Thai chili mayo. Both were amazing! If you want to avoid the wait, DuckFat does have a food truck that's a five-minute walk from their restaurant where they regularly serve the fries. We totally missed this sign but if we had seen it we would have done it to avoid the hour wait! // What to do in Portland, Maine in 8 hours

2) ENTREES: Get the brown butter lobster roll from Eventide. 

Most other lobster rolls are served cold but this one is warm, the lobster meat is extra succulent from the butter and overall it is absolutely amazing! We also got the lobster stew but I wish I had gone with some clam chowder. They also serve oysters some fresh from the Portland, Maine area I would definitely take advantage of these oysters if you can!! // What to do in Portland, Maine in 8 hours

3) Grab drinks from Portland Hunt & Alpine Club. 

They have a cocktail menu that has drinks that are either Refreshing, Adventurous, Classics, and Wild Card. SO FUN! I got the Clove Hitch which was great. The Lavender Collins was my second pick of the night! // What to do in Portland, Maine in 8 hours
Cocktail menu at Portland Hunt & Alpine Club

4) Get donuts from The Holy Donut. 

After getting a good night of sleep, we headed to The Holy Donut for breakfast. Our hotel actually served breakfast and we thought this would be the perfect opportunity to save some money, it would honestly have been overkill if we got brunch. However, if we had gone to Brunch The Bayside American Cafe would have been our first pick! // What to do in Portland, Maine in 8 hours // What to do in Portland, Maine in 8 hours
From top to bottom: Blueberry, Berry Cannoli, and Coffeecake

The blueberry donut was a seasonal one and had a 75 cent upcharge. My absolute favorite was the berry cannoli, the cream in the middle is this slightly sweet lemony tart cream that pairs perfectly with the berry donut. Seriously. It was AWESOME! 

5) Check out the Portland Head Lighthouse

Aside from the food, this was definitely our favorite part of our trip to Portland. The Portland head lighthouse has more than 3 miles of land surrounding it with amazing trails that you can spend a good amount of time walking on. The views are amazing and when the weather is nice, this place is the bomb. Every picture that you get of the lighthouse will honestly look perfect. 

There's a cute gelato stand on-site as well as a lobster roll food truck that probably opens close to lunchtime. You can definitely have a picnic enjoy the scenery here. It's beautiful! // What to do in Portland, Maine in 8 hours // What to do in Portland, Maine in 8 hours . // What to do in Portland, Maine in 8 hours // What to do in Portland, Maine in 8 hours // What to do in Portland, Maine in 8 // What to do in Portland, Maine in 8 hours // What to do in Portland, Maine in 8 hours

After getting a good amount of time at the lighthouse area, we headed back to the train station to purchase tickets and get back to Boston at a decent time to do the things we needed to do to get ready for the work week. Man, I usually don't experience Sunday Scaries but I was kind of feeling it that Sunday! Overall, it was an amazing trip because of the amazing company (shoutout to my hubby!), great food, beautiful weather, and a very cool city! 

If we had more time:

These are some of the suggestions we found that we would have done if we had more time! 
  • Explore Old Port 
  • Get baked goods from Tandem and an almond milk mocha 
  • Get late night cheap Thai from Boda after 9 PM 
  • Get brunch at Bayside American Cafe
  • Check out the Urban Farm Fermentory 
  • Walk the Eastern Promenade 
  • Eat a lobster roll by the water 
Have you ever been to Portland, Maine? What was your favorite activity to do there? Have you ever taken a spontaneous trip? 

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  1. Stoked to check out Maine!!!

  2. That looks like an amazing place! I want to go there too!

  3. Portland sounds like such a fun place to visit!

  4. I've never been to Portland, but I know I have some long lost cousins there. That would be a fun trip to go meet them and see these sights. Those donuts look incredible!


  5. Looks like such a fun time! I need to head to maine!

  6. Looks like a cute town-- glad you had the chance to visit!

  7. Portland looks amazing!! I want to visit there so badly!

  8. Wow! Y’all got so much accomplished! How awesome!

  9. Thanks for sharing such an informative blog. White travel is blogging now which provides everyone up to date on everything cruise related. I It is really nice one.
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