New England Coastal Road Trip Itinerary: Maine & Massachusetts Golf, Hiking, and Lobster Rolls
This August my husband and I traded the hot and humid Southern Illinois summer for cool coastal breezes, incredible seafood, and some of the best golf and hiking in New England. We both love to be active, so our trip was the perfect mix of playing golf, hitting trails, and finding the best local food. We also decided this will be a new tradition every August, and next on our list is exploring the Upper Peninsula of Michigan and Oregon.
Day 1: Arrival in Portland, Maine
We flew into Boston, rented a car, and drove straight to Portland. Originally we were flying directly into Portland, but we discovered our connecting flight was majorly delayed… so we had to pivot. Travel days: hope for the best, plan for the worst! We checked into The Westin Portland Harborview and crashed!
Day 2: Golf and Great Food in Portland
Breakfast was at Becky’s Diner, a Portland classic. We teed it up at Portland Country Club with a snow bird friend who is a member, which gave us the perfect introduction to Maine golf. Dinner that night was at Sicilian Table in Falmouth and it was incredible.
Day 3: Music Festival and Lobster Rolls
We started with a long walk around Portland, then grabbed lobster rolls at High Roller Lobster Co. The Back Cove Music Festival was the highlight of the day. One of our favorite bands, the Turnpike Troubadours put on an unforgettable show.
Day 4: Camden and Rockport, Maine
We had coffee and a pastry at Standard Baking Co. before driving north to Camden and Rockport. Lunch was at Claws, where the seafood was so good we ended up coming back later in the trip. After checking into Samoset Resort, we hiked Mount Battie. It was steep, rocky, and fun. (Although I was regretting eating so much lobstah! haha) Dinner at 18 Central in Rockport was outstanding.
Day 5: Golf at Samoset Resort
We played Samoset’s course, which has been called the Pebble Beach of the East Coast, and it lived up to the hype. The course is all along the coastline and fortunately for us it was not windy at all. After another lunch at Claws, we walked out to the lighthouse at the resort.
Day 6: Bath and Harpswell, Maine, then Gloucester, Massachusetts
We checked out and drove south, stopping for brunch at Mae’s Cafe & Bakery in Bath. We discovered the Cliff Trail in Harpswell and loved it. It was our favorite hikes of the trip.
That afternoon we checked into Beauport Hotel in Gloucester. Dinner was at Tonno and it was one of the best meals of the week. It’s within walking distance of the hotel.
Day 7: Exploring Gloucester and Rockport, MA
We spent the morning walking around Gloucester, then headed to Halibut Point State Park in Rockport. The coastal views were stunning. Lunch was a lobster roll at The Lobster Pool. FYI: Lobster Pool is BYOB, very casual but beautiful views out the back.
After some beach and pool time, we ended the day with a late dinner at Talise, a waterfront restaurant in Annisquam. It is small and intimate, so reservations are a must. We took an Uber there from the hotel.
Day 8: Golf and Newburyport
We checked out of Beauport and drove to Granite Links Golf Club in Quincy. It is a semi-private course, and we were lucky to get a last-minute tee time. It was absolutely worth the price and drive. It was out of our way (south of Boston) but we were so happy we got to play there. Be sure to go early so you can take advantage of their amazing practice facilities.
That evening we stayed in Newburyport at the Essex Street Inn & Suites. Newburyport is a must-see town with great walking trails, shops, and restaurants. This was the only leg of the trip where we back tracked a bit. Newburyport is north of Boston. Originally we were scheduled to play golf there, but after getting the last minute tee time at Granite Links, we just went with it. We were so glad we kept our reservations in Newburyport! We had a drink at Bar 25 and dinner at Carmine. They have wonderful Italian food. If possible, get a table outside because it was quite loud inside.
Day 9: Boston
The next morning we walked along the waterfront and the rail trail. We then grabbed a donut at Angry Donut and coffee at The Coffee Factory. I also heard from a local friend that Angie’s is THE spot for breakfast. Oon our way to Boston, we stopped in Beverly, MA to visit my friend and fellow FASTer Way coach, Emily Ogan.
In Boston, we checked into the Cambridge Marriott and took the metro to the North End. We had an early dinner at Neptune Oyster (be prepared to stand in line), best espresso martini in Boston at Bricco, and then saw Comedian Nate Bargatze at TD Garden. We ran (we really did!) to Mike’s Pastry after the show for a cannoli, which was crowded but worth it. The show ended at 9:30 and Mikes closes at 10:00pm. 😅
Day 10: Travel Day
We were up at 4:30 am for a 7:00 am flight home. The “re-entry” to real life has been tough. Laundry, groceries, yard work and back to the heat and humidity… My husband immediately asked what was for dinner. He’s lucky to still be alive. 😜
Let’s talk about my nutrition/fitness on this trip…
I didn’t track one spec of food on this trip. I ate French fries, enjoyed pastries, and ate bread! haha! I took time off from my workouts but still got around 15,000 steps each day. I slept great, took a couple of naps, drank water, and brought my supplements. Most importantly, I refused to feel guilty. (I will note that my skin and digestion do take a hit from eating this way!)
It was exactly the break I needed, but now I am ready to get back to my healthy lifestyle. The good news: It’s not a chore to eat healthier and lift weights. It fits right back in seamlessly.
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