Maine Travel Guide
September 4, 2018
Portland + Bar Harbour

maine travel guide

The other week Matt and I decided to pack our bags and head up to Maine for a little getaway. I had been to Kennebunkport last year and absolutely loved it and, in light of the crazy hot summer we have had, weather in the 70’s was sounding amazing. This time around we hopped on a quick hour flight from NYC to Portland, where we started our adventure. At the airport we rented a car, which made exploring parts around Portland much easier, as well as our road trip up to Bar Harbor.


< The Press Hotel >

For our first two nights in Portland, we decided to use our credit card points and stay at the Westin, which was fairly centrally located, but a little further from the main streets in town. Living in NYC, walking is never an issue, so we didn’t mind it. The Westin also offered a complimentary shuttle service (pick up and drop off) which we used when running late to dinner.

When we came back from our Bar Harbor road trip we wanted to check out a new hotel and ended up booking a room at The Press Hotel. It was awesome! While the room was smaller than the Westin, the hotel itself had so much charm and character and was steps away from the heart of town.


We flew in a bit later on Friday and by the time we arrived to our hotel and got settled, it was time for dinner. One thing to note in Portland (at least the time of year we were there) is that all the “good/well known” restaurants have a crazy long wait and many don’t even take reservations. We figured out how to “beat the system” after night one: we would put our name in around 5pm and then our table would be ready closer to 8pm when we would want to eat anyways. Yes, a 2-3 hour wait was typical! The crazy good food scene in Portland is apparently no longer a secret!  Matt and I love going to yummy restaurants so it is always worth the wait for us.

Friday night we struck out at a few places in the heart of town (if we waited we wouldn’t have eaten until midnight), but luckily we heard about Duckfat and ended up only having to wait 20ish minutes (the food was a quicker style bite) and indulged in our first decadent meal of the trip.  It was AMAZING! Do not go here without getting the Duckfat Fries and Original Duckfat Vanilla Milkshake. We rolled out of here, walked home and immediately crashed.

Duckfat Portland Maine

Fall Outfit Inspo

Fall Layers


We woke up ready to explore, but first stopped by Speckled Ax right by our hotel for a delicious cup of coffee.  We then made our way down a few of the streets, popping in and out of cute little shops. One of my favorites to peek around was Flea-For-All, which was a huge vintage flea market with so many different things. Folly 101 was also high on my list, their home decor/kitchen knick knacks were amazing!! I wanted everything, but had to restrain myself. Such a cute spot if looking to pick up a hostess item or two as well. A few others worth checking out are The Portland Trading Co.and Blanche + Mimi.

Folly 101

Folly 101 Portland

< Folly 101 >

Flea for All Portland

Antique Shop Portland Maine

< Flea-For-All >

The Portland Trading Co.

< The Portland Trading Co. >

After shopping for a bit we worked up an appetite and went to put our name in at Eventide. There was a bit of a wait, but not too bad (we hit this spot right before noon), so we put in her name and shopped a bit more until we were called. Eventide is an ABSOLUTE must! Their brown butter lobster roll is to die for and they have fresh oysters delivered  daily.

Later that afternoon, Matt and I grabbed our car and drove a short distance (about 20 minutes) out to Cape Elizabeth to see the lighthouse. The park and view on the water was beautiful and if you are still in need of lunch, they had a few food trucks and picnic tables you could grab a bite at.

Cape Elizabeth Lighthouse

The Lighthouse Portland Maine

Harding Lane Hat

Afterwards, on our way home, we stopped by Allagash brewery for a beer. They have a huge outdoor area and a food truck as well. Just an overall fun vibe to enjoy an afternoon drink.

Allagash Brewery

Allagash Brewery Portland Maine

Once we got back to the hotel we quickly changed for dinner and made our way into town. It was on the early side (about 5:45pm), but we wanted to try our plan for putting our name in early with hopes of then sitting for dinner around 8pm. This worked like a charm! We put our name into Central Provisions and then walked around a bit and grabbed a cup of chowder  from Gilbert’s Chowder House right on the water. We then grabbed a drink a the cutest spot, which was once famous for their non-alcoholic mocktails, but has since incorporated alcohol to their menu. This spot was called Vena’s Fizz House and 100% worth checking out! Matt and I both agreed our favorite drink was from the original mocktail menu, Blackheart and the waitress recommended to add bourbon! This spot also prides themselves on their mixologists and even has an entire room you can shop with tons of different bitters, mixers, etc. to make these cocktails at home. Around 8:00pm we were texted that our table was ready and headed back to Central Provisions and enjoyed a tapas style meal. Definitely ask your waiter/waitress for their favorites, ours hit it spot on!

Central Provisions Portland

Sweater Dress

Mocktail Bar in Portland Maine

Vena's Fizz House


Sunday morning we got up early, checked out, and headed out on our coastal drive to Bar Harbor. We decided to take Route 1 the entire way, stopping at different points and towns along the way. We were in no rush , so it was so nice taking our time and enjoying the drive and scenery.

Route 1 Maine Drive

Our first stop was in Freeport where we did a little shopping. The LL Bean outlet along with many others are located in this town. Next on our mini road trip was stopping at Red’s Eats in Wiscasset for lunch. They are known for their lobster rolls, each of which is  stuffed with a pound of lobster. They open at noon, and when we got there at 11:30 there was already a pretty long line, but it was worth the wait! From start to finish we were in line for about 1 hour, but the staff once were more than accommodating. They came around with fried shrimp samples, umbrellas to block the heat and water. After lunch we continued north stopping in Rockland, Rockport and Camden Hills State Park for a view. We arrived to Bar Harbor at about 5:30pm, just in time to check out the property and enjoy sunset by the water.

LL Bean Outlet Maine

Red's Eats Maine

Best lobster roll in Maine

Maine Lobster Roll

Rockport Maine

Maine Coastal Drive

Bar Harbor Maine

Route 1 Drive Maine

Camden Hills State Park

Camden Hills State Park Maine

maine lobster rolls

In Bar Harbor, we stayed at the The Harborside Hotel. The property is amazing. Located right on the water and steps from town, it truly had everything. Two pools on the property, two hot tubs, tennis courts and fire pits. Such a perfect hotel for relaxing and enjoying the beauty of Bar Harbor.

Bar Harbor Hotels

Where to stay in Bar Harbor

The Harborside Hotel Bar Harbor


For dinner, we walked around the main street and ended up at Side Street Cafe. The nachos we spilt as an app were delicious and Matt enjoyed his meal. To be honest, I think I just ordered terribly because I wasn’t thrilled with mine. This spot is super family friendly (Bar Harbor in general is) and a fun little atmosphere with indoor and outdoor seating.


We woke up early hoping to beat the rush at Acadia National Park. We grabbed a quick bite on the go and coffee in town and drove theshort distance to the park. The entrance fee was $20 per vehicle and you can opt to drive all around the park to the different lookout points (most people including us did this) or hike. Make sure you grab a map so you hit all the locations and also grab a popover and blueberry lemonade from Jordan’s Pond House when you are walking around Jordan’s Pond.

Jordan's Pond

Acadia National Park

Jordan's Pond Restaurant Popovers

After the park, we made our way back to the hotel and enjoyed some much needed pool time. When lunch rolled around we walked next to the hotel to grab a lobster cobb salad from Stewmann’s Lobster Pound which was delicious. We then made our way for an ice cream cone at Mount Desert Ice cream. We were also told to try a whoopie pie, which we picked up before heading back to the pool.

Bar Harbor Waterfront

lobster cobb salad

Stewman's Lobster Pound

free people pullover

Maine Whoopie Pie

Bar Harbor Sunset

For dinner we were hoping to get into Havana, which is known as Martha Stewart’s favorite restaurant in Bar Harbor. Luckily a reservation opened up and we were able to snag it! Nestled off the beaten path we dined and enjoyed some of the yummiest dishes. Once again we asked the waiter for his recommendations and went off of that.

Bar Harbor Maine


We grabbed a quick (and YUMMY) breakfast from a well known spot called Cafe This Way. Make sure you get there early or else you will have to wait! Matt and I split the blueberry pancakes (a must) and an egg scramble. On our way back to Portland we decided to take the more direct highway route, since we already explored the scenic route. Once back we checked into a new hotel, The Press Hotel, which would hands down be my recommendation for staying in Portland.  Such a cute hotel with fun decor and located right smack in the middle of town. The room was a bit smaller than the Westin, but I enjoyed the overall vibe much more. Once we settled in we walked down the street to grab a few donuts from The Holy Donut. I was waiting all week for this and they did not disappoint! I wish I was eating one as I write this! We tried the dark chocolate sea salt (my favorite), lemon (they were out of Maine blueberry) and maple bacon.

Cafe This Way Bar Harbor

The Holy Donut

Trying not to spoil our appetite for dinner, we made our way down to the waterfront to put our name in to J’s Oyster. It is an old school establishment known for their fresh seafood. Matt and I both had clam chowder and split a lobster salad. To wash down our lunch we then stopped by Liquid Riot for a beer. A fun little brewery also on the water with a few games inside and indoor and outdoor seating.

Portland Maine

Later that day we made our way back to our hotel and got changed for dinner and our last night. We put our name in at Street & Co and snagged a 8:30pm reservation. While waiting for our table we grabbed a drink at Blyth & Burrows, which was hands down my favorite bar. They have a “secret” back room behind a bookcase that you can ask to sit in, but the overall vibe is just awesome. Once again they have mixologist whipping up yummy cocktails and great small bites to eat as well.

blyth and burrows portland

Dinner at Street & Co was exactly what I had in mind and was craving. A cute and cozy restaurant where I enjoyed linguine and clams in a white wine sauce and Matt tried the wood oven lobster with linguine. We both really enjoyed our dishes!

The next morning we had a 6am flight back to NYC so Matt could drop off his bags and go right into work. We do this often, and even though it makes for an early morning, it allows us to maximize our time on our trip. If you have any questions about our little road trip let me know! Will definitely be back to Maine soon to explore more of this state!

Advertise OnStyled Snapshots
Get Started