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  • Writer's pictureRay Cheselka


A trip to New England at the peak of fall is a must for anyone who enjoys foliage. After our wedding we wanted to do a minimoon (#corona), so we decided on Maine, New Hampshire, and Vermont.

This was both of our first times in the Northeast, and now that the wedding was done we were looking forward to relaxing. These states are so peaceful and beautiful. You get that crisp, fresh fall air you expect-and of course some of the best seafood you can get.

For this trip, we spent 3 days in Maine, 2 days in New Hampshire, and 2 days in Vermont. It's a bit of an aggressive itinerary. If you wanted less driving and a slower-pace, you could easily simplify or extend this trip.


  • Day 1: Fly into Bangor, ME around dinner time. Get food to go. Relax at a cozy Airbnb.

  • Day 2: Drive to Bar Harbor, ME, where Acadia National Park is. Explore the park, shop, eat lobster. Drive to the hotel near Boothbay Harbor, ME, get dinner downtown.

  • Day 3: Watch the sun rise in Boothbay Harbor. Get breakfast, shop, explore Boothbay Harbor, go on a whale-watching cruise. Drive to Portland, ME. Explore, eat, and drink in downtown Portland.

  • Day 4: Explore Portland. Shop, eat a lot of seafood, go see a lighthouse and the coast south of Portland. Drive to the hotel at the foot of the white mountains. Eat dinner and drink at the hotel.

  • Day 5: Drive and hike around exploring foliage, taking pictures, soaking in views. Another dinner at the hotel.

  • Day 6: Driving to Burlington, VT. Stopping along the way in Woodstock. Seeing the Sleepy Hollow Farm and Vermont countryside. Dinner downtown Burlington.

  • Day 7: Walk along the Burlington waterfront, soak in the views, get coffee. Head to the airport to fly home.



The morning after our wedding, we woke up and headed to the airport. We flew from Cleveland to Philadelphia for a quick stop, and up into the northeast. Ready to relax.

Upon landing, we picked up our rental car and made our way to the Airbnb. Maine was particularly strict at the time we visited with COVID. They even had metal signs outside of the airport with protocols, and we had to make a reservation for Acadia National Park. We were tired so we decided to pick up some carry out and enjoy time together in our cozy Airbnb. We got Mama D's Thai Restaurant. it was really good! We watched some TV and got a great night of sleep ahead of an early drive to Bar Harbor, and Acadia National Park.


Waking up, we made some coffee and got on our way to Bar Harbor. The clouds were dense and low that morning, and the colors on the rolling hills created a great contrast to the grey skies. We couldn't have gotten any luckier with our timing.

Arriving in Bar Harbor, we wanted to get some coffee before heading into Acadia. By the time we got to Bar Harbor, the overcast was burning off and it was turning into a crisp, sunny fall day on the Maine coast. We walked through the town, and ended up getting coffee at the Pink Pastry Shop. They had a lot of good sweets, and really good coffee too. This was our first Whoopie Pie sighting, and it was evident that wild blueberries are a favorite to the locals.

Onto Acadia National Park.

Pro Tip: We have an annual national parks pass, they're a great deal at $80 if you plan on going to a few National parks. A day pass alone is $30.

We loved the vibe of this national park. It was easy to navigate. Parking was plentiful once you got past the first lot. If you wanted to hike, there were tons of trails. If you felt like just cruising through the park, stopping in certain spots for a bit, it was very easy to do that too. This park is so unique because it has dramatic rocky cliffs covered in colorful trees that bump right up to the coastline.

Recommended Hike: Beehive Trail - moderate level- about 2-4 hours

We started at Sand Beach. This dramatic coastline is exactly what you'd imagine when you think of the Northeast. When looking out at that ocean a calm just comes over you while you take deep breathes of the freshest air. If you hang out for a while, there are some pretty cool fishing boats that you'll see pass by.

We were told Cadillac mountain was a must-see, and it lived up to the hype. Incredible 360-degree views from the Ocean, to the inland.

After exploring the park, we went back into Bar Harbor for our first Maine Lobster Roll at Side Street Cafe. We ordered lobster rolls and our waitress said she "had to go check if they'd finished preparing this morning's catch". Needless to say, the lobster rolls were delicious. The clam chowder on the side was as warming and tasty as you'd expect it to be. We also had a great local Maine Blueberry Beer on draft that had fresh blueberries in it.

After lunch, we walked around town, got some sweatshirts, and started on the road down to Boothbay Harbor. Once we arrived at Linekin Bay Resort, we settled in and got ready to go into town for dinner and drinks. This resort was really nice and had a great view of the bay. Due to COVID the normal activities and on-site dining were closed. However, we enjoyed the peace and quiet.

They have a variety of lodging options. We stayed in the king waterfront room. The homes you can rent on the property also seemed really cool if you're considering staying here.

Boothbay is a small town, so options were limited, but we found a great spot called The Boathouse Bistro Tapas Bar and Restaurant. It was warm, great service, and the food was outstanding. Our waitress made a great recommendation for a bottle of wine we really enjoyed-Rustenberg-Stellenbosch Chenin Blank-2018-South Africa.

We called it a night and got back to the resort for a great night of sleep. We were excited to go on a whale watching tour in the morning, see more of Maine, and eat more seafood!

Day 3-Boothbay, ME, Whale Watching, and exploring Portland, ME

Waking up, Maddie caught a beautiful sunrise at Linekin Bay Resort, then we got ready and went into town for breakfast at Waves. Our crab benedict and pancakes, along with coffee they frequently come around to refill, got the day off to a great start.

We did some souvenir shopping here, and then boarded the boat to try and see some whales!

While we didn't see any whales (we did see some sea lions towards the end), it was incredible to be in the Atlantic Ocean far off the coast of Maine. The air is so fresh, the boat was selling really good local beer, and we felt like we were really starting to relax and enjoy ourselves. If you go on one of these tours (we went in October)-layer up! It can get cold.

Pro Tip: They also told us that the warmer months are most ideal for seeing their local wildlife. In the summer months, you can often see puffin penguins, whales, and sea lions.

Upon returning to Boothbay, we grabbed some dirty chai lattes and a blueberry muffin at Red Cup Coffeehouse. We both agreed that they were some of the best chai lattes we've ever had! We later saw this coffee at a coffee shop in Portland. We parked in a lot that was $8 for the day, once we finished our snack we returned to our car and started to drive to Portland.

We got to our hotel in Portland, The Press Mariott Autograph Collection. The Press is a really nice hotel with super comfortable beds and a rainfall shower. On top of this, it's in a prime location in the heart of downtown and has a great restaurant and bar in the hotel.

After getting ready, we went out to a restaurant we were glad was recommended to us, Street & Co. It was in the fisherman's wharf in this old brick back alley. Great vibe. The weather was perfect, and we had an outstanding meal. I don't think you can go wrong here. Maddie's Scallops were the highlight.

After Street & Co., we went back to the bar Inkwell at the hotel. The bartender was really nice, and we had a few "Purple Haze" cocktails. We, unfortunately, didn't get a chance to take advantage of the happy hour, but it seems like they have some really great deals. EX: Friday Lobster Roll and glass of wine for $10.

And that was all she wrote!

Day 4-Portland, ME, Great Food, and Drive to New Hampshire

This day was dedicated to walking around Portland, and eating delicious food. Maddie ended up getting a hat, we had lobster on a stick, poutine, oysters, we saw a classic Maine lighthouse on the ocean, and it rained, need we say more?! We were seriously so thankful for how well this trip worked out!

We slept in a bit, got ready, and walked down to the Wharf, eventually making our way to Duckfat. The poutine was SO good, they had a lobster panini special of the day and other things to pick from but relatively a smaller menu (snack bites). We stuck to beer and poutine so we could hop around and try a bunch of different food. We wanted to go to Eventide Oyster Company (recommended to us) but the wait was 3 hours! Seems like it must be really great. I'd plan on putting your name in then walking around to kill time until a table is ready.

We needed a pick me up after the heavy poutine, so we went to Coffee By Design. This is where we saw the Red Cup blends for sale. Really nice people, simple coffee shop. We enjoyed some drinks and made our way to find some more lobster.

We ended up near our hotel at The HighRoller Lobster. SO GOOD. Maddie had a Lobster roll and I had a variety of local oysters, with lobster on a stick and a side of lobster infused butter. Wow, too good. Everything on this menu looked great. We couldn't get enough seafood in Portland.

Back to the hotel to grab our things and car, and then we went to see the Cape Elizabeth Lighthouse. It was windy and cold right on the Atlantic, but quintessentially Maine. It started to rain so we got in the car, and made our way to central New Hampshire, to The Glen House at the bottom of Mt. Washington.

We loved this place. The comfiest bed with the softest sheets. Full mountains covered in foliage out of our window and in the main lobby with a bar, and a restaurant with good food. All we needed. On the first night, we grabbed a late dinner and had a couple of bottles of Pinot Gris! The crab cakes here were our favorite, along with the pot roast. It was a long day, so we got to bed for a great night of sleep.

Day 5-Exploring New Hampshire and the White Mountain National Forest

With all the travel on this trip, it was nice to have a couple of days in the same place. We took it really easy here and just cruised around through the forest. The fall colors were so vibrant here, it was like nothing we've ever seen.

We started the day with breakfast at the hotel, and then drove all around the White Mountain National Forest, pulling off to soak in views and take pictures. The northeast countryside and mountains are breathtaking and simply peaceful.

We wanted to take the Mt. Washington Auto Road to the summit, but conditions were too harsh. Apparently, it is one of the windiest mountains in the USA. There is also a railway on the other side of the mountain. Due to the weather, we felt it wasn't worth paying to do the railway but on a clear day, it would definitely be a great activity to add to the list.

We ended the day by drinking wine and eating at the hotel again. I know I know, kind of boring, but we were exhausted and the convenience of just being able to walk back to our room was appealing! (Due to COVID, a lot of restaurants were closed so it was easier to eat at our hotel as well).

For anyone that wants to stay at The Glen House but check out other food/neighboring towns, North Conway was the biggest town nearby with options of shopping and food.

We drank, reflected on our wedding and enjoyed each other's company!

Day 6-Woodstock, VT, Sleepy Hollow Farm, and the Vermont Countryside to Burlington, VT

Back on the road and now we're headed to Vermont! Our first stop was Sleepy Hollow Farm near Woodstock, VT. Definitely a bit of a tourist trap, but it's off the beaten path, and being in the Vermont countryside was just beautiful. This farm made us want to own some land like that one day. There were some backroads you could take that separated us from the crowd.

Honestly, these backroads were some of the best scenery we saw the whole time!

We stumbled upon this beautiful piece of property that ran alongside the main road. We pulled over to take a picture and this lady pulled up right next to us and told us that she owned the property. She was so friendly and told Maddie that she could take pictures of whatever she wanted! She continued on to tell us how she had a bunch of animals, a shed where she harvested her own maple syrup from the trees on her land and that she uses this property for her extended family to come and stay throughout the year. It was truly amazing listening to her talk about the history her land endured, while admiring the charming land.

Meeting people like this on our trips is one of the main reasons we love traveling so much. Learning how other people live is incredible. It makes you appreciate the small things in life.

After taking some pictures we went into town and stopped at the Woodstock general store F.H. Gillingham and Sons while waiting for a table at Dr. Coburns Tonic. You could get souvenirs, locally made items, and essentials. We got some blueberry syrup, maple syrup, blueberry pancake mix, and a few other things.

For lunch, we had a lobster roll and burger. Very good and really nice service. Our server was a young girl from Boston, she was in college and told us how she comes to Woodstock on her breaks to get away from the fast-paced life of Boston and live within nature. Before continuing on to Burlington, we shopped around the quaint little town and made a quick stop in Stowe.

Arriving in Burlington, you realize even Vermont's biggest city is a pretty small town. We went into the main street in town called "Church Street", most of which is blocked off to cars. It's loaded with shops and restaurants. We messed up by not making a reservation on a weekend night. We ended up getting fish n chips, and a salad with creme brulee at Sweetwaters American Bistro. We enjoyed sitting outside and people watching.

If you make a reservation or go on a weekday, Leunig's Bistro, Pascolo, and The Farmhouse Tap & Grill were recommended to us.

We called it a night and returned to the Homewood Suites. This hotel was okay, had a good breakfast, good location in between downtown and the airport. Mountain views.

Day 7-Burlington, VT, travel back home

Even though our trip was ending, we were excited to see Burlington in the daylight. We were in awe at Lake Champlain. Walking on the lakefront (Battery Park, and Waterfront Park), we just stood there and soaked in the views of the Adirondack Mountains behind Lake Champlain.

It was nice to enjoy the view, fresh air, and reflect on a great trip. We are always so thankful that we can make these trips happen.

Our friend Cait sent us some money as a "honeymoon treat" to get some coffee (thanks Cait!), so we went back up to Church and Pearl to get Kru Coffee Collective. It was packed, clearly a local favorite. You could get CBD in your coffee, and they seemed to have good pastries too.

We walked down pearl and headed to the airport. Such a small airport! Back to Ohio, we went, before heading back to Denver.

A phenomenal trip it was.


List of things to get ahead of the trip:

  • COVID-check current requirements by state!

  • Flights

    • Your hometown to Bangor, ME (or another hub)​

    • Burlington, VT to your hometown or next destination

    • We paid about $250 each on American, with 1 stop each way (Philly, Charlotte)

  • Rental Car

    • Costco Travel

    • Expect around $300 for a week-long trip

  • Hotels/Airbnb’s

    • Bangor

    • Boothbay Harbor

    • Portland

    • New Hampshire

    • Burlington

    • Estimated Total: $750-$1000

  • Other

    • Whale watching tour: $138

  • Save some money. We saved estimating we'd spend around $200 per day of the trip. If you have the money ahead of the trip, it really gives you peace of mind. You can do everything you want to, and know that it's essentially paid for.

    • Estimated Total: $​1,400

  • TOTAL ESTIMATED TRIP COST PER PERSON: $1,869 per person (that includes everything)

Some things to pack:​

  • A range of clothes light/warm-weather can change quickly with the mountains/coast

  • A blend of hiking/casual/dressy clothes

  • You don't need hiking boots, but some solid tennis shoes or boots would be ideal

  • Reusable water bottle

  • Backpack (we have REI flash 22 pack)

  • Emergen-c (take care of your immune system ahead of and on travel days!)

  • Sunglasses

  • Sunblock

  • Hat(s)

  • Neck pillow

Some things to check:​​

  • COVID restrictions

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