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Portland Paradise

When kicking off my Take 12 Trips Challenge this November, my decision to start in Portland, Maine was an easy one. Visiting for the first time three years ago on a sporadic getaway with my mom, I fell in love with the small city along the coast with a laid back vibe, innovative food scene and thriving art culture. Once a warehouse and merchant capital, Portland has been revitalized and has blossomed into a prominent, modern city while still retaining its architecture, cobblestone streets and industrial roots. It has received numerous accolades in the last few years including most livable city, foodiest small town and seventh greenest city in America.

I have been itching to get back since that first visit and my weekend in Portland did not disappoint. Portland is the perfect weekend getaway and offers an array of activities for every interest. Here are my recommendations for taking in all that Maine’s largest city has to offer in just two days.

Day 1

Start by stopping at Portland Head Light on your way into town. Located 15 minutes outside the downtown area in Fort Williams Park, Portland Head Light is the perfect place to experience a quintessential Maine lighthouse with a view. The beautiful fall morning saw minimal visitors, while the unexpected sunshine allowed for spectacular coastline views.



Making your way downtown, lunch should be your next priority. In a city dominated by award-winning chefs and locally sourced cuisine, choosing where to eat will be one of your toughest decisions. As a French fry aficionado, I highly recommend Duckfat, the casual restaurant serving salads, sandwiches, soups, milkshakes and of course their signature, duckfat fries. While the fries were the highlight of the meal, the paninis did not disappoint either. Max’s pastrami special and my Portobello mushroom, butternut squash with gruyere cheese panini were both fantastic.

duckfat fries

Walking off lunch is essential, so continue your way through Old Port neighborhood. Filled with boutiques, galleries, restaurants, and other local specialty shops, this area will keep you intrigued. Once you are done admiring this revitalized warehouse district, make your way down to the water for views of the harbor and the smell of the salt air.



In a city with a plethora of breweries and microbreweries, deciding where to try the best beer can be a challenge; however, for me it was a no brainer as one my favorite beers is brewed and bottled in Portland. The 20 minute drive from downtown to the Allagash Brewery was well worth the trip to see the newly expanded facility. Tours run every hour on the hour from 11am-4pm and are free; however, you will need to book a spot ahead of time as tours fill up quickly (especially on Saturdays). There is a bar area outside the brewery that offers all visitors four 3oz. flights before or after your tour. Allagash White, Curieux, House and Four were on tap for the day, which are some of their best!

allagash brewery


Returning back to town, walk around and take in the city at dusk. Gorgeous sunset views are to be had over the water and since the holiday season is fast approaching, white lights were strewn about the city streets when we were visiting.

Prior to dinner, we stopped in at Street & Co. for a pre-dinner drink. While I have heard great things about their food, we chose not to spoil our appetite before dinner and settled into a cozy bench in the bar area. Many people chose to eat in the lounge or wait for their party in the bar area, so it was warm and lively when we were there. The brick walls and rounded archways make you feel like you were in someone’s living room and Street & Co. was the perfect place to relax before dinner.

Dinner in Portland is a tricky decision, but we finally settled on Fore Street, one of the gems of the Portland dining scene. I had been itching to get to Fore Street since my last trip to Portland 3 years ago when it had been closed for a private event. Walking into the brick building, you immediately feel cozy as the restaurant opens to a wood-burning oven and partrons can watch the chefs at work in the open kitchen. You will not be able to find a menu online as it changes daily based on the availability of local ingredients. The food is cooked to perfection and I am still dreaming about the best mussels I have ever consumed. Oh and did I mention the pumpkin gingerbread cake with strawberry ice cream for dessert? Our experience wholeheartedly committed us to a return visit to Fore Street in the future.


fore street dessert

Day 2

If you eat as much as we did in Portland, an early morning walk along the water is the perfect cure. On your way grab a coffee and pastry from Standard Baking Company. Located underneath Fore Street, this Parisian style bakery with standing room only produces some of the best pastries in Portland. With a cute awning and a handful of tables outside, it is a great spot to enjoy your coffee in the warmer weather; however, if you are looking to move like we were, take your coffee and walk the Eastern Promenade Trail. This waterfront trail is a peaceful way to start the morning complete with fantastic harbor views and connections to other trails.


eastern prom

Returning from the Eastern Promenade Trail, make your way to the Victoria Mansion, a national historic landmark, for a tour. This Victorian-era museum is noted not only for its architecture, but also for the importance of its interior design. The Victoria Mansion is only open from May – October and then it opens again for the Christmas season. When I visited three years ago, I was fortunate enough to see it decorated for the Christmas season and would highly recommend visiting then if you can time it properly.


After your morning of walking and touring you will probably be hungry again so make sure you fit in another one of Portland’s staples: pizza. Many will debate the “best” of Portland pizza: Micucci’s, Otto, Flatbread Co., Vignola, the list goes on; however, Flatbread Company has long been one of my favorite pizza restaurants with no locations in Boston. (I also love Otto, but with multiple Boston locations I knew I could get this at home). After a long internal debate, I settled on the Flatbread Company, casual and cozy with an open kitchen exposing the pizza ovens.  You can bet that I will be putting Micucci’s and Vignola on my list for next time though!

flatbread co

Lastly, make your way to the Portland Art Museum. Featuring American, European and Contemporary art along with special exhibitions and varied programs, the museum is not to be missed.

As you can see this waterfront city provides the perfect blend of attractions for any visitor – art, food, breweries and shopping among the most popular. This revitalized industrial city has proven that it has the sophistication of a big while still keeping everything local.


Portland is only a two hour drive from Boston and a five hour drive from New York City. Portland International Jetport is located just 15 minutes from downtown Portland and services Delta, JetBlue, Southwest, United and US Air.  Ferry is another popular way to arrive and depart with the Casco Bay Lines providing passenger and car transportation.

Both times in Portland have found me at the Portland Regency Hotel & Spa. Located downtown, it is the perfect location for walking to restaurants, shops and museums as well as being within two blocks of the water. The rooms are spacious, clean and reasonable while the staff is friendly and attentive.


Have you been to Portland? Are you planning on going? What are your recommendations? 

14 Comments Post a comment
  1. Horace #

    Bridget, Portland has always been on my list too! After reading about all the fun things to do as well as the FOOD!!!!! I’ll be moving it up my list! Thank you for the great depiction of this wonderful city!

    November 21, 2013
    • Thank you! Yes, the food is definitely one of the main attractions! There are so many talented chefs and innovative restaurants, my only regret was not being able to try more. I already have my list ready for next time. Hope you make it there soon!

      November 21, 2013
  2. Bridget, the pictures SOLD me and convinced me that I need to put Portland on my trip to-do list. Aside from the architectural beauty, I think the major selling point was the pumpkin gingerbread cake and, of course, drinks from a mason jar!

    November 22, 2013
    • Thank you! We were so fortunate to have a beautiful weekend. Yes, the food and drink (and presentation) have such an innovative twist in Portland. Such a fun city, I hope you make it there soon!

      November 22, 2013
  3. If ever I’m seriously hungry, I’ll have a good idea where to head, Bridget 🙂

    November 26, 2013
    • Yes, Jo! Portland is one of the foodiest cities in the US. And breathtaking by the water. I hope you make it there!

      November 26, 2013
  4. Kristen #

    I know who to find when I need some help planning weekend getaways 🙂

    December 8, 2013
    • Absolutely! Weekend getaways are the best to plan because you only need to fill a relatively short period of time. Happy to help if you ever need assistance!

      December 8, 2013
  5. Dana #

    Bridge, I can’t wait to stop by Portland. A close easy destination that sounds like so much fun!!

    December 14, 2013
    • Thanks, Dana! It really is a great city and is an easy ride from Boston. I hope you make it there soon!

      December 14, 2013

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