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New England Trip: Maine

It had always been on my dream bucket list to stay in a bed and breakfast in a New England state in the fall, sit on a cozy porch overlooking the mountains and the colors, and my dream came true!

My husband and I got married in May and delayed our honeymoon until October so we could take this special trip to the New England states to see places neither of us have seen during what we hoped was peak fall season. We stayed at great places, ate great food, drank great coffee, met great people, and we saw some of the most brilliant colors we’d ever seen! A huge shout out to Alexis Drago at Born to Roam Travel for planning all of our flights and lodging. She did an amazing job of taking what we envisioned and making it happen!

This article is about our days in Maine and has our itinerary at the bottom with links. I’ll share a separate post about New Hampshire and Vermont after this. Pictures follow each section below of that venue or excursion and then our scenery photos from Maine are at the end. We believe we were about a week of Maine’s peak but it was still absolutely beautiful!


We flew out early so we arrived in Portland late morning. This gave us the entire afternoon to check out downtown and enjoy our hotel. Our first two nights were at The Press Hotel which is a part of the Marriot system. It’s theme is vintage writers, thus the name, and the decor reflects that with old typewriters adorning the perfect spots, letters and writings on the walls and carpet, great quotes tucked everywhere, it was so fun and still elegant! Sorry for all the detail photos below but I love quotes!

Our only disappointment with The Press was that their famous restaurant, The Union, was closed the days we were there. But we were able to enjoy their bar, The Inkwell, which served delicious coffee and treats for breakfast, drinks and small plates for dinner, and their servers and bartenders were out of this world! It was there we met a barista and server, Morgan, whom we just loved, and B decided we should adopt her. She was so much joy and told us a lot about the area and where we should go. It was so helpful! Hello to Morgan if you’re reading this!

The Press:

NOTE: When planning this trip or any trip, keep in mind that a lot of places are closed the first part of the week.

After checking in The Press, which is so beautiful and in the heart of downtown Portland, we had our first meal out on the trip. The Highroller Lobster Co. downtown, which appeared to be a cute sandwich shop, but we had a wait of almost half an hour to get in! That means it’s good. B wanted Maine lobster right away and he loved their lobster roll! Not being a big seafood eater, I had their huge BLT with jalapeno mayo and it was delicious too! Great relaxing atmosphere, friendly staff, and fresh food. Worth the wait!

We relaxed at the hotel for the afternoon and had a light dinner downstairs in The Inkwell. There we met a great couple who knew a lot about the area (she was a professional downsizer, how cool is that?!) and they shared lots of information with us for our trip. And we then met a couple who actually live in NC just 30 minutes from us, what a small world! Always a joy to meet new people! Hello to Heather and John!


We spent our first day looking for lighthouses! We visited the Portland Head Light, Bug Light, and Spring Point Ledge Lighthouse. While they are all worth seeing, our favorite was our first – the Portland Head Light. We said wow about 1,000 times! Unfortunately, their website is down, but I am sharing pictures below. It was breathtaking and we felt like we were on a movie set! The lighthouse, the ocean, the waves crashing in on the rocky beach… beautiful! And we were able to climb down to the water and take in the view even more. Just the sounds of it all were breathtaking in addition to the view.

Bug Light was smaller, the architectural elements were beautiful, and it was an easy walk to the light. Spring Point was totally different and unique, a little bit more of a walk over flat rocks, but doable for almost anyone who is steady on their feet.

During our lighthouse excursion, we stumbled on our lunch location on the water, The Lobster Shack. I will say it felt like a hole in the wall at first but had rave reviews and there was a line waiting for them to open their doors at noon. That says a lot! And it is not a hole in the wall, it’s a quaint and lovely little place, with gracious staff, amazing food, and outdoor seating right beside the ocean! B had the haddock basket and I had shrimp and we were both so happy with how good they were!

That evening before dinner, we relaxed at The Inkwell and had The Pressman’s Ink drink – it was grey (how weird!) and so good! Then it was off for our reservations at Evo Kitchen & Bar, an easy walking distance from our hotel. It was hard to get reservations but was worth the effort. We arrived to be given champagne as B had stated on our reservation that we were on our honeymoon! We enjoyed their retro cool atmostphere, along with their fun and delicious cocktails, Thyme of Your Life, Can You Fig It?, and Build Me Up Butternut! I mean who doesn’t want to try drinks with those kind of names?! They were delicious as was our food. The best part was the chef bringing our dishes to the table explaining the ingredients or how they were cooked. So fancy and fun.

DAY THREE – Tuesday: Portland to Bar Harbor

We had coffee in our gorgeous lobby at The Press, just sitting by the fire. We met a wonderful man from Texas who had coffee with us and told us he didn’t give a hoot about seeing a bunch of leaves but his wife of 35 years did so there he was! LOL. He was wonderful! Hello to Trey if you ever read this!

This was our day to leave Portland for Bar Harbor and most of the day was spent driving and seeing the colors. It was so beautiful and every chance we got, we’d pull over to little areas where there were no official overlooks so we could be on our own.

On the way to Bar Harbor, we found another lighthouse, the Rockland Breakwater, and decided to stop. It – was – one of our favorites! Note, it is almost a 2 mile hike from the parking lot out to the light and back, walking over a lot of flat rocks with some good size crevices in between, so you really have to be steady on your feet and enjoy a good hike. And the view on the hike out is beautiful!

From there, we continued on our way and were excited to stop for lunch at a place that came highly recommended, Red’s, but it wasn’t open (that first of the week thing again) so we wound up across the street at an outdoor walk-up seafood hut called Sprague’s Lobster. It was good, not our favorite, but good. We did meet a guy whose son had gone to UNC and enjoyed talking to him!

Again on the road to Bar Harbor and enjoying the gorgeous scenery, we decided to find a cute coffee shop – that’s one of my things but I’m converting B:) That’s when we went through the adorable town of Camden and found the Owl & Turtle Bookshop! Good coffee, good people, and books – what more could you ask for?!

We finally made our way to our next lodging, the Harbour Cottage Bed & Breakfast. It was wonderful and had several cozy sitting areas and a fireplace, a small charming bar, an outdoor covered porch for dining, and another outdoor area with a firepit. The cottage also had a chef for breakfast and small plates for dinner, and they offered evening drinks, where I had my first ever chocolate martini, and I loved it! You know me and chocolate!

Once we got settled in, we went to dinner nearby at Eat a Pita/Cafe 2. What a welcome surprise! Vintage, quirky, almost fine dining, and the food was wonderful! We were actually craving salads so we both had salads and B had clam chowder while I had tomato bisque soup. The salads were beautiful and full of good stuff and the soup was amazing. We did learn you typically need reservations so we were fortunate to even get in! It was full.

Back to the B & B for the evening and the end of our day three.


We spent the bulk of this day seeing the sites, buying our lifetime pass to the National Park system, and riding through Acadia National Park. I wish I could tell you how truly beautiful this park is but words cannot describe it. You have to have reservations to go to the top of Cadillac Mountain within the park as they only allow so many visitors every hour. I love that! It allows you to do a bit of hiking out on the rocks and see the entire site without as many people. There are other websites for Acadia which show more photos but the one above and below are the official sites. This one of our favorite places of our trip.

Our lunch was in downtown Bar Harbor which was a great little town but being a cruise port, it was very crowded. We were able to get into Stewman’s Lobster Pound for a delicious lunch!! The crowds kept us from really staying and seeing the town so we headed out to see more colors and relax at our B & B. That night, we had a light dinner there, and met two wonderful ladies who lived in the neighborhood and dropped in for appetizers and a drink. One was a realtor and one was formerly a NY stock broker whose family went back generations in Bar Harbor and she was retired there and living in her ancestral home. What a joy to meet them!

DAY 5 – Thursday: Bar Harbor to New Hampshire

A lot of this day was also spent enjoying the colors and stopping on bridges, climbing down to rivers surrounded by color, and just taking it all in. Around lunchtime, we googled restaurants close by, and found The Highland Grille in a little town called Turner, Maine. GPS was taking out to the middle of nowhere until we came up on a golf course. Highland was at the entrance to the course and we were hungry! We met a lovely and fun lady, Joyce, who was running the place, and she was so joyful and helpful and the food was out of this world! Another favorite meal of our trip! Hello, Joyce, if you ever read this!

After leaving Highland, and just before leaving the state of Maine, we found what is called Sunday Bridge ~ Artist’s Covered Bridge in Newry, Maine. It was so pretty and definitely worth stopping to see and take pictures. From there, we continued on towards New Hampshire, and just after entering the state, we discovered the Dermody Road Artisan Coffee House in Gorham. It was really quirky inside, so cute, and decorated for Halloween, and the coffee was delicious. We had our drinks outside with a 10 foot skeleton, lol, and just enjoyed taking a break.

We were finally in New Hampshire, the most colorful state of our trip!



THE PRESS HOTEL, Portland, Maine

The Highroller Lobster Co.

The Lobster Shack

Portland Head Light (no website currently)

Bug Light

Spring Point Lighthouse (Note, this is a long hike out to the lighthouse but worth it!)

Evo Kitchen & Bar


Rockland Harbor Lighthouse

Sprague’s Lobster

Owl & Turtle Bookshop (Camden, ME)

Eat a Pita/Cafe 2

Acadia National Park and Cadillac Mountain

Stewman’s Lobster Pound

The Highland Grille (Turner, ME)

Sunday Bridge ~ Artist’s Covered Bridge

Dermody Road Artisan Coffee House


Just a few scenery shots throughout Maine!

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  1. Tracy,

    Great job of putting this all together. You’re re-living your trip to share with us – but I recognize the work you did putting it together too. Beautiful photos and descriptions of your travel. Can’t wait to read more about your trip.

    1. Oh gosh, thank you so much for saying that!! It was a lot putting this first part of the trip together in this article but it was great to relive it too, such a blessing to get to go!! Thank you, as always, for being here and commenting!!

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