A New England Adventure: Boston To Bar Harbor Favorite Must-See Stops and More

We finally did it! A visit to New England has been on our bucket list for many years. Although I’m not a travel blogger, I wanted to share some impressions from our Boston to Bar Harbor road trip. I’ll share where we stayed, dined, and our favorite stops on our New England adventure.

First, we had planned this trip for our 40th wedding anniversary in 2019, but my mom’s health was failing, so we postponed the trip, and then the pandemic hit. We finally said enough is enough and started making plans just before our 45th wedding anniversary. I enlisted the help of my New England friends Jennifer at Cottage on Bunker Hill and Ann from Dabbling and Decorating. They both said the beginning of September, just after Labor Day, would be perfect. With our desire to see the coastline, stop at quaint restaurants, and do a little vintage shopping, the weather would be good and less crowded.

So we boarded a plane for Boston on September 7th and arrived at 9:30 am to spend the day exploring Boston! Here’s how our trip progressed.

Day 1 – Boston, MA

We wanted to make the most of every day on our trip, so we flew out at the crack of dawn to arrive in Boston at 9:30 am. This allowed us to get a good taste of this bustling city.

We stayed in the Seaport, South Boston Waterfront District, which was amazing. We learned the area has undergone major renovations with new restaurants and hotels. The streets and sidewalks were filled with outdoor enthusiasts walking and jogging alongside their furry companions.

The architecture was unique and jaw-dropping. This was a view from our hotel room.

Faneuil Hall Marketplace

We also ventured into the more established downtown area of the city to visit Faneuil Hall Market Place. My friend, Heidi from Eleanore Rose Home lives in the Boston area and recommended we visit. The marketplace is filled with restaurants, street vendors, and shops. Plus, there were many street performers and musicians. As a bonus, Brad found this Cheers door for a great photo opt.

As we walked the streets of Boston, we saw activity on every corner, and we were impressed with how the community seemed to embrace their city. We walked over 8 miles exploring, with a few stops along the way. See more about where we stayed and dined.

Where To Stay

We stayed at the fabulous Seaport Hotel in the Seaport Neighborhood. It was conveniently located and within easy walking distance of many great restaurants. I would highly recommend this hotel. Our experience was first class.

Where We Dined

One of the top priorities when we travel is to find great restaurants. So we began with lunch in Boston. We found a great-looking location along the waterfront called Woods Hill Pier 4. The view was amazing, but to be honest, we were underwhelmed with our meal, and it was pricey for a burger and sandwich. However, we didn’t have seafood, which might have been a better choice. Afterward, we walked to Faneuil Market Place and wished we had waited to have lunch there. There were so many great-looking spots.

After that 8-mile walk, we stopped in at SAVR for a refreshing beverage. We really liked the atmosphere and location. We checked out the dinner menu, which looked great, but we had already made dinner reservations elsewhere. However, if we had more time, I’m sure we would have had a meal there.

Dinner was at Strega Italian Restaurant. It had a cozy and intimate atmosphere, and the food was delicious. We had no regrets about keeping the reservation.

All that walking increased our appetite, and after returning to the hotel, we decided on an after-dinner drink and a snack at TAMO Bistro & Bar. It was a busy and fun late-night spot, and our service was incredible.

Day 2 – York & Ogunquit, Maine

On day 2, we traveled from Boston to York, Maine, to meet my friend Ann for lunch. She had suggested an outdoor venue at the Viewpoint Hotel. It was an incredible location with a view of the Nubble Lighthouse at Cape Neddick. The food and the company were amazing.

After lunch, we got a close-up view of the lighthouse and visited Ann’s home. This was my first time meeting Ann in person and it was so fun to see her coastal Maine home and to meet Ella.

Then, on to the overnight destination, Ogunquit.

Ogunquit, Maine

Ann had mentioned some points of interest in Ogunquit, so once we had checked into our room, we began to explore Perkins Cove. It was a short walk from our hotel, and we enjoyed the views and quaint shops. After more walking, we began to look for our dinner location. More about that later.

The following day, we walked the Marginal Way Trail, a highlight of our trip. The 1.25 cliff walk offers some incredible views of the Maine coastline. I have to share some of my favorites.

In addition to the rugged and beautiful coastline, Marginal Way includes a close up view of Lobster Point Lighthouse.

Where We Stayed and Ate In Ogunquit, Maine

We stayed at the Grand Hotel, which is centrally located within walking distance of both ends of Ogunquit. The property is older but immaculately maintained. Our room was a suite with a large balcony and was very comfortable. Parking was free, and I would stay at this location again.

We had dinner at The Maine Catch, next door to our hotel. I had Lobster Risotto, which was probably my favorite meal on the entire trip. Brad had Chowder and Crab Cakes, which he also loved. We had a wonderful experience having dinner in the bar and chatting with other diners. Everyone was so friendly and helpful.

Before leaving Ogunquit, we had breakfast at Perkins Cove Kitchen, which was as impressive as our previous evening dinner. It was a quaint little restaurant with outdoor seating.

Day 3 – Camden, Maine

After leaving Ogunquit, we traveled up Hwy. 1 to make the most of our New England Adventure. We took a detour through Kennebunk Port to see the sights. Therefore, we didn’t arrive until later in the afternoon.

We walked into the beautiful downtown Bay Area and explored the shops and restaurants along the waterfront. We were a little surprised that many of the restaurants were closed for the evening. However, we found a cute Irish pub, Cuzzy’s, and had an afternoon drink and snack.

We discovered that the Rooftop View Restaurant at 16 Bay View was open for dinner, and we had the best evening enjoying the view and eating small plates from cozy side chairs.

The next morning, we decided to explore some more and foolishly chose to hike the Mount Battle Trail. At the tail head, it said there might be some scrambling. The trail is 1.1 miles, but the elevation is close to 600 ft. Which basically means straight up. LOL. It really wasn’t the elevation that got me; it was the walls of straight-up rocks that we had to climb. I did okay going up, but my recently developed fear of heights caused some scary moments navigating the slick rocks coming down. But we did it, and even my Kate Spade crossbody bag survived being slammed into the massive rocks multiple times.

Afterward, we had a leisurely lunch before heading off to our next New England Adventure.

Where We Stayed In Camden, Maine

The Riverhouse Hotel is within walking distance of the bay area of Camden. It’s a great location, but it could use some updates. It was clean, and everyone was extremely helpful, but it was my least favorite stay on our trip.

I’ve already mentioned our fun snack at Cuzzy’s and the amazing views at 16 Bay View Rooftop. However, before leaving Camden, we had lunch at Waterfront Restaurant, which has a huge deck overlooking the bay. I had a delicious crab melt, and Brad enjoyed chowder.

Day 4 and 5 – Bar Harbor, Maine

The next day, our New England Adventure had us traveling up Hwy. 1 in search of Bar Harbor, Maine. We once again took a detour.

Fort William’s Park, Cape Elizabeth – Portland Head Lighthouse

This was a perfect stopping point for walking along the cliff trails and enjoying some refreshing gelato from the food trucks set up in the park.

Portland Head Lighthouse is the oldest and most photographed in Maine, and I probably took a hundred photos myself. LOL

We finally made it to Bar Harbor and checked into our motel, which I’ll share later. We quickly refreshed and took the shuttle downtown for our dinner reservations.

A Sailboat Tour and Harbor Exploring.

The following day, we decided to explore the surrounding areas. We drove to Southwest Habor and visited the Bass Harbor Light Station. It was hard to get a good photo because it sits right on the cliff edge. We made a wrong turn and accidentally took a scenic route through Northeast Harbor and saw some beautiful coastline.

That afternoon, we booked a two-hour sailboat tour around the many small islands surrounding Bar Harbor. It was amazing to see how many lobster buoys were on the water. In addition, we were fortunate to spot a couple of small whales and a porpoise. They didn’t stick around for any photo opts, but it was exciting to see them nonetheless.

Where We Stayed In Bar Harbor

Funny story alert. Upon arriving at our destination, we were a little dismayed to find that Highbrook Motel was what we called a motor lodge from another era. We even drove by saying this can’t be it. But apparently, this was where we had made our two-night reservation. We had already checked in online and had our keyless entry code. So we came back and parked right in front of our door. Wow, were we surprised? This was the cutest room, and everything was immaculate. The location was within a mile of downtown and was an easy walk, but in addition, they provided a free shuttle to downtown, and a complimentary breakfast was delivered to our room each morning. We would highly recommend Highbrook Motel if you are ever in the area. It was a blast from the past, but so well done.

We had dinner reservations at Geddy’s Seafood Restaurant on our first night in Bar Harbor. Since we got downtown early, we had a pre-dinner drink at Paddy’s Irish Pub. Both locations were lively, and our food was delicious. The seared haddock and fish and chips were both delicious.

Because we liked Paddy’s atmosphere and harbor-view outdoor seating, we had Fish Tacos for lunch there the next day before our sailboat excursion. We also loved their blueberry Mojitos so much that we stopped by after the excursion for another one.

For our final night in Bar Harbor, we had dinner at The Thirsty Whale Tavern, where I had my first Lobster Roll, and Brad had the haddock ruben. Both were yummy. The restaurant was slightly off the beaten path, which we enjoyed because we found Bar Harbor more touristy than expected.

Day 6 – Portland Maine

On day 6, we arrived in Portland, Maine, mid-afternoon. After checking into our conveniently located hotel, we immediately began to explore the historic downtown and harbor area. The old buildings and brick walkways were charming, and we stopped in at several interesting shops. We discovered the Port Hole Restaurant along the water and enjoyed a beverage while listening to live music and harbor views.

Where We Stayed And Dined

Upon arriving in Portland, we checked into the Marriott Courtyard, which was located in the Downtown Waterfront District. The location was excellent; it was easily within walking distance of all the shops and dining areas, had first-class accommodations, and had a friendly staff.

For dinner, we ate at Scales Restaurant, which was highly recommended. Although we didn’t have a reservation, we were able to sit on the patio. This was a blessing because all the tables were dimly lit and cozy, unlike the loud and much brighter indoor dining area. For an appetizer, we had the best Mussels we’ve ever tasted. Some main dishes were pricey, and I don’t recommend the salmon. Brad had Fluke, a new fish to us, and he loved it. If you are ever there and weather permits, request patio seating and have the mussels.

For breakfast the next morning, we were told we had to try the potato doughnuts at Holy Donuts. After waiting in a long line, we carried our large donut (we decided to split one) to the water’s edge to enjoy our breakfast. They were good, but not as good as Krispy Creme. LOL ,

Before leaving, we had lunch at Boone’s Fish House and Oyster Room, a lively harbor-view restaurant with lots of outdoor seating. We enjoyed more Maine Mussels and harbor views before heading south.

Day 7 – Portsmouth, NH

It’s hard to believe this was our last stop before heading home. Where did the week go? But we were so happy with our final destination. Portsmouth, New Hampshire, is filled with charming harborside restaurants and shops, which is precisely the New England experience we had hoped for. There were many restaurants and shops, but they did not have the tourist feel we had experienced in some of the areas.

We were able to walk from the hotel to the downtown area and explore the shops and points of interest. We were once again drawn to the restaurants along the river. There were several to choose from, and we stopped at the River House for some close-up water views and refreshments.

One highlight of our Portsmouth stay was visiting with my friend Jennifer from Cottage on Bunker Hill and her husband, Chuck. They treated us to a typical New England night out. First, they picked us up at our hotel and had dinner reservations at the Oar House. The restaurant was quaint with a very old-world vibe. The building was built in 1803 and had so much character, like the hole in the floor next to where we were seated. I wondered what was down there and learned it was a spring-fed well that served the needs of the original grain warehouse.

They also have a covered outdoor area across the parking lot if you prefer to sit outside by the water.

Where We Stayed In Portsmouth, NH

We had another great hotel experience in Portsmouth, NH at the AC Marriott. Just like the Courtyard in Portland, the accommodation was first-class. There was a rooftop bar with a great view of the harbor, where we enjoyed a late-night after-dinner drink. We wanted to extend our last night for as long as possible.

Our meal at the Oar House was excellent, and I’d highly recommend the restaurant for anyone visiting the area. Brad enjoyed fish and chips while I had a delicious haddock piccata dish.

Day 8: Portsmouth And Traveling Home

On our last day before traveling to the airport, we decided to have a late brunch. We were directed to The Friendly Toast, which was another fantastic experience. All the retro tables and decor enthralled my vintage-loving heart. Plus, the food lived up to the hype. Brad’s Armageddon omelet and my goat cheese, bacon, and mushroom scramble may have been the best breakfast ever. No kidding.

We had time to stop in at a few more vintage and antique shops as we made our way back to Boston. This was one of my favorites, and the gentleman was so lovely. When we told him about our trip, he was so encouraging about traveling while we were still able and not waiting until it was too late. He had lost his wife a few years ago and told us he didn’t want us to miss a moment but to get out and enjoy life.

We had been putting off this trip for five years, and we had said the same things while making our plans. We may never get the chance if we keep putting off our bucket list. I didn’t get his name, but the shop was in New Hampshire, and I think it was called LaPointe Antiques. It was his daughter’s shop.

New England Adventure: Conclusion

We made so many beautiful memories on our New England Adventure! The trip has many highlights, but I’ll share a few. We could not have traveled at a better time. The weather was perfect. The lowest mornings were in the mid-50s, and afternoons ranged from the 60s to the 70s. I didn’t wear short sleeves until we reached Portland, where the high was in the low 80s.

All the flowers were stunning, and I’ve never seen so many hydrangeas everywhere.

Last impressions and tips.

• First, our favorite place on the trip was Ogunquit, Maine!

• Best Hotel Experience: Seaport Hotel, Boston, MA.

• Favorite Meal: Rachel – Lobster Risotto at the Maine Catch, Ogunquit, and Brad – Fluke and Mussels at Scales, Portland.

• Favorite Cocktail: The Blueberry Mojito at Paddy’s Irish Pub in Bar Harbor

• My favorite Lighthouse Experience is a tie between Nubble Lighthouse at Cape Neddick and Portland Head at Cape Elizabeth.

• Meeting Ann for the first time and spending time with Jennifer and her husband were also high on our list.

• The craziest thing we did was climb Mount Battle in Camden, Maine.

What would we do differently? We drove most of the trip on Hwy. 1, and the traffic was slow. I would hop on and off the turnpike instead of staying on Hwy. 1. I also loved stopping at the vintage shops, but air travel prevented me from buying. If you love vintage shopping, you might want to make it a road trip.

Thank you for stopping by, and I hope this encourages you to travel if it’s on your bucket list.