Travel Tuesday with Taylor to Portland, Maine

Posted on Travels with Taylor June 6, 2017 by Taylor Deer

A New England Summer Kickoff in Maine

by Taylor Deer

Celebrating New Beginnings in Maine

Happy June! As many of you know, I love June. Yes, it is my birthday month, but it is also the start of a new summer season. I have always seen this month as chance for new beginnings. Not only do I turn a year older on June 25, I also always tend to start something new in my life during this month.

I will be turning 26 this year and instead of glooming over it because I don’t necessarily feel “ready” to approach my later twenties, I decided to celebrate the start of this new age by lighting my hair for the many wonderful trips I have planned. (Thank you to my brother’s girlfriend Maria for the new hair. If you are in NJ, make sure to head to Core Salon in Randolph for a new hairdo!) In addition, I also bought my first big girl camera – a Nikon D3400!

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Life is looking great on the blonder side!

The start of my upcoming adventures was spending Memorial Day Weekend in the Portland, ME area. I have been to Vermont for ski trips and Connecticut because it is so close to where I live, but I had never fully experienced true New England. There is something about winding cobblestone roads, streetlamps and peaceful seaport beaches and fisherman villages that make New England poetic. I couldn’t wait to go and experience a new place!

My best friend Courtney (who also loves traveling as much as I do) and I decided to do a girls weekend together and made the five and a half hour road trip to the artsy city of Portland. We arrived later in the afternoon and after checking into our hotel, we couldn’t wait to head into Old Port, Portland’s downtown area. Portland is a funky seacoast town that offers award-winning restaurants, cocktail joints, history and art!



Our First Night in Old Portland
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Excited to explore Portland!

We could not wait to immerse ourselves in fresh seafood dinners, buttery lobster rolls and delicious craft beer and cocktails. Dinner took us to a warm and welcoming waterfront restaurant on Commercial Street called Boone’s Fish House & Oyster Room. When we arrived in Portland it was cold and rainy, so Boone’s was a great place to warm up since they have several fireplaces and a great selection of Portland-brewed beers. For dinner, I ate a delicious crab roll on a brioche bun and Courtney had lobster mac and cheese! All of Boone’s seafood is fresh and delivered right to the restaurant. Are you drooling yet?

The night took us through history as we made our way around the cobblestone streets. Our first stop of the night was at Vena’s Fizz House, a corner-side cocktail house with a charming turn-of-the-century atmosphere. Vena’s offers a plethora of drink options for all ages that features fresh ingredient fizz drinks that are both alcoholic and non-alcoholic along with mocktails and cocktails. The adorable bar even has a boutique that offers Vena’s mixology of syrups, infusions and other ingredients to create your own craft cocktails at home.

The best part about Vena’s is that their drinks aren’t too strong. I know everyone has his or her drink preferences, but I cannot enjoy something when all I taste is alcohol. I ordered a Maple Syrup Switchel, that consisted of rum, fresh Maine maple, molasses, ginger, coffee and aromatic bitters. I was able to savor every flavor and it was unforgettable!

After enjoying some time at Vena’s and getting to know the friendly owners. We took the party over to a local Portland bar on Commercial Street called 3 Dollar Dewey’s. This great beer bar reminded me of the 1980’s sitcom that took place in a local Boston bar called Cheers – “where everyone knows your name”. While we were at 3 Dollar Dewey’s, we got to meet friendly people from New Hampshire and even got to snack on popcorn, a treat the bar offers to its guests. Needless to say, our first evening in Portland was a success!

But First, Coffee and then Brunch!

Our second day in Portland was absolutely gorgeous. We wanted to take advantage of the sunny weather, so we headed back into Old Port to walk around and grab a freshly brewed cup of coffee at Coffee by Design on Congress Street.

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Beautiful Old Portland!

After walking around the neighborhoods and admiring all of the cute New England architecture, we were starving for a delicious breakfast. Portland is known to have many great brunch spots, so we had many options to choose from. Since we were in the area, we stopped at an adorable farm-to-table gastro-pub called Little Tap House. When we walked inside, all of the furniture pieces were rustic and the decorations were colorful and charming. It was the perfect welcome after a rainy first day. Courtney and I both enjoyed a mimosa and had the best meal to go with it. Courtney had the sweet Belgian French Toast and I had a savory breakfast bowl that consisted of home fries, caramelized onion, locally sourced mushrooms and peppers, scallions and topped with fried eggs.  The breakfasts we both had were out of this world! I definitely recommend this wonderful spot when you visit Portland.

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The Cutest Brunch Spot in Portland, Maine!

Strolling Around the Promenade

Once we finished brunch, we were both so full that we had to walk around the city. We walked down Congress Street, through a few neighborhoods, before we hit the Eastern Promenade – a breathtaking coastal trail, built along an old rail corridor that offers beautiful views of the harbor and Casco Bay. Since it was a gorgeous day, there were plenty of sailboats in the water, people hanging out on the lawn and East End Beach and, of course, their adorable puppies playing in the chilling water. This 2.1-mile trail allows people to bike, run, bird feed, dog walk and enjoy the day. You can even take a train ride around the promenade and learn more about this wonderful seaport city.

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Admiring the natural beauty around me on the Eastern Promenade in Portland.

The Lighthouses!

The afternoon took us over to South Portland to see the lighthouses. Even though I have spent every summer down the shore, I had never seen a lighthouse in real life. There is one in New Jersey on Long Beach Island, an hour south from where I usually go to the beach in Lavallette. (I need to make my way there at some point.) The first lighthouse we saw was the Spring Point Ledge Light, right off the Southern Maine Community College campus. (How lucky are those students to have a campus with a lighthouse?)

The Spring Point Ledge Light is a dangerous obstruction on the west side on the main shipping channel. Unlike many of the lighthouses, this tower is built of brick instead of cast-iron and is located at the end of a 900-foot breakwater. The large pieces of rock allow you to easily walk across the breakwater to the lighthouse. Unfortunately, on the day we went, we were unable to tour the inside of the lighthouse, but it was still cool to walk up to it and enjoy the views of the harbor, pebble beaches, historic forts and the beautiful Casco Bay. I definitely recommend wearing comfortable shoes when you walk across the breakwater because there are a lot of ways you can fall and twist your ankle. We had a great time taking pictures on the rocks and watching the boats pass by.

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It was a bit windy on the breakwater, but it sure was beautiful!

After our time at Spring Ledge Light, we drove 15 minutes into the affluent town of Cape Elizabeth to the stunning Fort Williams Park. The beautiful park features 90 acres of rugged beauty along the Casco Bay. There are several hiking paths with beautiful cliffside views of the water crashing onto the rocks. (See, you can still experience rocky coastlines on the east coast!) There are many great lookouts, a rock beach, picnic areas, a playground, ball fields and more!

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Breathtaking Fort Williams Park in Maine!

As you continue to walk south, you can catch a stunning view of the symbolic Portland Head Light modeling its beauty on the coastal cliffs of Cape Elizabeth. The Portland Head Light is located at the head of the primary shipping channel into Portland Harbor. Gazing out at the lighthouse reminded us of why we chose to come to Maine in the first place!

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This is how I pictured Maine to look like!
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The best lobster rolls in Maine!

Before coming to Maine, I read on a few travel blogs that the best lobster rolls were found in a small food truck in Fort Williams Park called Bite Into Maine. Since the truck is so small, we had a tough time trying to locate it, but it gave us the opportunity to explore the park more and interact with the locals. We finally found it and indulged in amazing, fresh Maine lobster chunks on a fresh bun. We felt like we were in a New England heaven!

Saturday Night in Downtown Portland

Since we had the amazing lobster rolls in the afternoon, we weren’t in the mood for a heavy dinner. I was recommended by my fellow yoga friend Dina (of Yoga with Dina) to check out Gilbert’s Chowder House right off of the wharf on Commercial Street. I was in the mood for a warm soup, so I was excited to give it try! I ate a delicious New England Clam Chowder in a freshly baked bread bowl. It was the perfect light dinner and Gilbert’s offers a warm and welcoming atmosphere.

The night took us over to Bull Feeney’s a fancy Irish tavern located on Fore Street that offers something for everyone. On the bottom floor, you can grab a drink and sit down at one of their tables and talk with friends. The second story features a dance floor with a room off to the side that hosts Maine’s best cover bands. You can even get seated service and enjoy a lovely Irish brunch or dinner.

Adventuring through the Southern Maine Beaches

A downside to this trip was that we didn’t make it to the famous Acadia National Park in Bar Harbor, ME since it was four hours away. We did, however, explore the beautiful beaches south of Portland to make up for it! The next morning, we drove a half hour south to grab breakfast in Old Orchard Beach. This wonderful beach town is family oriented, has a fun boardwalk and even has a nature preserve and private beaches to relax.

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Looking out at Old Orchard Beach.

Afterwards, we made our way down to Biddeford Pool, a secluded coastal town with beautiful cedar houses and a breathtaking rock beach. Even though it was Memorial Day Weekend, there wasn’t a soul around. It was awesome though because we weren’t stuck in the many tourist traps beach towns tend to carry on summer holiday weekends.

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The Rock Beach in Biddeford Pool.

We walked around the rock beach towards the white sand beach. The cool part about these beaches is that they have a small hiking trail through woods and meadows that you walk through to get to them. It was beautiful and we got to see a lot of birds and even do some yoga!

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Peaceful Warrior in Peaceful Biddeford Pool

Our next adventure led us to the adorable small town of Kennebunkport. There was a beach just as beautiful as Biddeford, except there were more people. Even though it is spring, there were so many colorful trees surrounding the beach area. I definitely would love to come back during an upcoming fall season.

The weather was pretty cold, so both Courtney and I were craving a warm drink. We headed into downtown Kennebunk to grab a warm beverage at a cute coffee shop and explored Main Street before heading back to Portland.

Since it was our last night in Portland, we wanted to get a nice dinner on the water (of course consisting of something lobster-related). We were able to enjoy a beautiful sunset and delicious lobster rolls (for one last time) at DiMillo’s Restaurant and Lounge. The night took us back to Bull Feeney’s and then we enjoyed a fulfilling dessert at Gorgeous Gelato, across from the bar.

It was raining pretty hard the next morning, so wanted to get on the road early. We first stopped at The Holy Donut located in Old Port before hitting the road. Their donuts are delicious and are made with locally grown potatoes! It was tasty, unique and the perfect way to end our time in Portland.

I hope you all enjoyed reading about my adventures in the Portland, ME area. I definitely recommend everyone visit Maine this upcoming summer if you are looking for a peaceful getaway. The beauty of this state and its awesome array of “foodie” options did not disappoint me!


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Visit Maine!

If you have any questions regarding my trip to Maine, please send me an email at I hope you all have an amazing summer and do something new and exciting!

Happy Travels!


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