New England Leaf Peeping in One Week

A whirlwind autumn itinerary checking the highlights and then some

COVID19 came and conquered 2020. Needless to say, all of our travel plans came to a screeching halt and I had to improvise my annual birthday trip. Instead of four new countries this year, I decided to see four new states and discover New England. I’ve always wanted to see the rainbow of fall leaves and mountains in this corner of America but other exotic and international destinations always took priority. It was the tail end of peak season when I made up my mind so I crammed months worth of planning into 48 hours. One gift the pandemic gave me was cheaper-than-usual hotel rates and flights so I had that going for me. Dormant Marriott Bonvoy points came in handy too.

Before I dive in my itinerary, here are some resources that will help you out when you’re ready to plan your own. There’s an interactive foliage prediction map / visual planning guide (yes, really!) that will give you a good idea of what to expect when you’re chasing colors. I’ve been told by locals that you work your way down from north to south, west to east. That means Maine, Vermont, and New Hampshire usually peak late September to early October and Massachusetts, Rhode Island, and Connecticut peak mid-late October.

If you decide to tackle Acadia National Park, their official site will come in handy with park updates and closures. The week before I arrived they were pilot testing parking passes due to overcrowding and social distancing.

Finally, Boston Magazine and will be your expert guides, Yelp will be your best foodie friend, and TripAdvisor will be your travel bible.

Oct 15–22

Day #1: Boston, MA to Hanover, NH

By the time I landed in Boston and picked up my rental car sunset was only two hours away. My first night’s stay was in Hanover, New Hampshire and I wanted to catch a bit of color so I wasted no time hitting the road. Some start their trip by heading north to Maine and going west, but since I was already late to the leaf peeping game I did the opposite to maximize my chances.

It was dinnertime when I checked in my hotel and I turned to trusty Yelp for recommendations. I found Molly’s Restaurant & Bar as one of the few places open for business and realized it was right in front of Dartmouth College when I pulled up. Being so close to the campus surprisingly gave me strong nostalgic vibes and I pondered what it would take to get a Masters at an ivy league. I stopped in a local DVD and vinyl shop on the way to my car and end up chatting with the owner for half an hour. He told me stories of celebrity Dartmouth alumni who used to be regulars and showed me all the vinyl he was giving away for free. His 20 year old establishment was relocating to another part of town and I just happened to be there for its closing week.

The next morning the area was lively with breakfast-goers and students. I recommend grabbing a quick pastry or coffee at Lou’s on your way out.

Day #2: Hanover, NH to Burlington, VT

It would be a rainy but beautiful day to Vermont. Crossing Ledyard Bridge in the morning, I saw a couple of kayakers and pulled over to capture the trees’ reflection in the Connecticut River.

On the way to Woodstock, VT you’ll pass the Vermont Antique Mall (worthy of a stop!) and Quechee Gorge Village right next door. I wanted to hike down the gorge with my camera, but it started pouring so I decided to carry on. I’ve come across many “come for the food, stay for the view” recommendations for The Mill at Simon Pearce, but skipped it this time due to the weather.

If you’re looking for the ultimate drive take Route 100, the Scenic Byway. This will lead you to the popular SugarBush Farm where you can taste test all of their award-winning cheeses and pure Vermont maple syrup. I brought some back home with me. Billings Farm & Museum is also a must-see if they’re open (they weren’t during this time due to COVID19).

Woodstock is a great spot to sleep over for the night or to spend a full day wandering around. Plenty of antique and art shops line up along Old River Rd as well as dine-in establishments and cafes. I don’t know how it came about, but I found myself detouring off Route 100 towards Bethel, VT and found a piece of private heaven between Charlie Wilson Rd and Camp Brook Rd. Here was a golden forest with nothing but the sound of heavy raindrops, rustling leaves, and my footsteps swishing them around. I’d make Burlington, VT my home base for the next two nights and explore the surrounding areas.

Day #3: Stowe, Smuggler’s Notch, & Burlington

The sun came out to play and we had a perfect day. My first stop in the morning was the official Ben & Jerry’s factory in Waterbury on the way to Stowe. Normally they provide tours, but this year was obviously different. Still, you can visit their Flavor Graveyard year round with no admission fee.

Stowe is a favorite among many, and its quaint and lively personality shines through the locals and attractions. I would definitely recommend a full day or two dedicated to this town — my agenda was to spend more time in Smugglers Notch State Park for hiking and nature photography. I did the Bingham Falls Trail and it was the perfect backdrop for some tripod selfies. I loved this area of the park for its stillness and closeness to water. People were sunbathing on the large boulders and kids were in tow with families. It’s a spiritual place.

I got a good drench of fall color this day between the drive to Stowe and Smugglers Notch before heading back to Burlington. I soaked in the remaining sun at Harbor Marina with a maple and butter crepe and hot apple cider from The Skinny Pancake. This area is perfect for dates and families — there was plenty of opportunity for people watching, listening to live music, and snack tasting along Waterfront Park. Church Street Marketplace and the Red Square can’t be missed if you make it to downtown Burlington. I really enjoyed Vermont. It may be a new annual tradition.

Day #4: Franconia, the White Mountains & Conway

Another day with too much to do and too little time, I kick-started my morning early for Franconia. Follow Route 100 to US-2 in Danville for fields of farms and smokey mountain views. You’ll pop on I-93 which will bring you to Lincoln, NH where you’ll find Franconia Notch State Park. It’s hard to miss the White Mountains in front of your windshield. I wished I had two more full days to explore here. This area was probably my favorite place (and apparently for many others too) to hike and experience all the natural wonders I wanted: foliage, sun, and surprisingly snow! Get here early in the day to beat the crowds. It was busy and it wasn’t even peak season anymore.

Once you get your fill of Franconia, stop in Woodstock, NH for lunch and dessert. Yes, there is another Woodstock on this itinerary! I have friends in the area who choose Woodstock, NH as home-base for their hiking excursions to Franconia and the White Mountains (called “Land of Many Uses” on its national park signs) so this is a great recommendation. Woodstock Inn Brewery is perfect for burgers, beer, and beds.

Keep going on the scenic Kancamagus Hwy (Route 112) towards the White Mountain National Forest. I took the Lincoln Woods Trailhead where I crossed a suspension bridge to bask in the surroundings and take photos.

I couldn’t stay long as I had another hour’s worth of driving to my next destination and didn’t want to miss the sunset in North Conway. I come to find that this neck of the woods had the most abundant and vibrant foliage on my tour. Note to self: North Conway is where it’s at for my next future visit. I chose to stay at a private Airbnb tucked away in Whitefield, NH to save driving time and money. I would wake up at 5am the next morning to conquer the 5 hour drive to Acadia National Park. Many people say Acadia deserves its own separate timeline and dedicated itinerary, but I tend to push the envelope and decided to go since I was in the Northeast already. I have no regrets.

Day #5: Bar Harbor & Acadia National Park

The drive from Whitefield, NH to Bar Harbor would be the longest leg of my journey. I’m so grateful I started super early because dawn shows you prime conditions for fantastic photography. Driving east, I encountered frosty mist and heavy fog first before a velvety magenta sunrise peeked over the hill. I took my best and favorite shot along highway US-302 E at Pleasant Pond.

If I were to do this trip over I would add on an extra day to explore these tiny pockets of civilization in rural southern Maine. These lands remind me of the abandoned human hideouts in apocalyptic / zombie movies. You’ll be safe here when the world ends. ME-11 N to ME-122 E, then 1–95N to US-1A will bring you to Bar Harbor where you should spend a couple nights or more. By the time I got to the entrance of Acadia it was noon. I wasted no time getting out of the car and onto a trail. I wouldn’t check in my hotel until that night.

I don’t where the energy came from, but I would do the Jordan Pond trail, Ocean Path, Bass Harbor, and Cadillac Mountain all in the same day. I DO NOT recommend this to anyone because you’ll want to take it all in and the only way to do that is to take it slow. I had no choice because I had limited time and I wanted to take advantage of the perfect weather. People were right — Acadia deserves at least three full days especially if you’re paying the $30 park admission which is good for 7 days. Trust me, I wish I had stayed longer.

Jordan Pond is an easy 3.4 mile trail with elevated log boardwalks which makes for a different kind of hike. The walkway is narrow so be prepared to stand to the side or jump off for traffic coming from the opposite direction. The popular Jordan Pond House sells hot popovers to lines of tourists while the gift shop next door sells park souvenirs and admission passes. I bought my postcards here first before starting the trail. At the end there’s a perfect place where I was lucky to have it all to myself. This is where I wrote my postcards.

It was a much needed breath of fresh air from the long drive. This would be another zen moment from my trip. Next was the Ocean Path walking trail which consists of Sand Beach, Thunder Hole, and Otter Cliff. This is a top rated attraction for Acadia tourists— it definitely was mine! If you love the ocean like me, you’ll want to visit these spots over and over again. You’ll find Ocean Path along the 27 mile Park Loop Road. The road will take take you around Mount Desert Island and is worth looping at least once. I did it twice.

Standing at the edge of Otter Cliff is where I realized how ignorant I ‘d been about the northeast coast and its glory and beauty. I was deeply moved. I wished I had my parents with me. I imagined sharing this with someone I’ll be in love with one day. I wondered if I’d still have the drive to travel this far when I’m old and grey. I was in my element and my cup was full.

I wanted to see what Bass Harbor Head Lighthouse looked like in the afternoon light so I headed south after I finished Ocean Path. It’s about a 40 minute drive from Cadillac Mountain. I’d arrive around 4pm and sun would set at 5:45pm in Acadia.

The lighthouse was smaller than I anticipated and parking was full. I had to wait about 15 minutes for a spot to open before I could step out of the car. By the time I finished taking pictures I was almost out of steam— I only had coffee, an energy bar, and a couple of cookies since that morning. A quick Yelp search for “lobster rolls” brought me to Charlotte’s Legendary Lobster Pound in Southwest Harbor, about 7 minutes from Bass Harbor. Their slogan is “Home of the World Famous ‘High-End’ Lobster” but don’t let that fool you — this takeaway-only lobster shack is far from highbrow and prices are reasonable considering you’re kind of remote on a southeast coast island.

I grabbed my to-go lobster roll and took off for Cadillac Mountain. Everyone says this is THE SPOT to get the best sunrise, but also not too shabby for a sunset. My fingers were getting numb from the cold air when I found a good set up for dinner with a view. I tried to do a time lapse of the sunset but a family of four unknowingly photobombed me. You can still get the idea.

As darkness and temperatures fell, I cranked up the heat in my car and headed to Bar Harbor for dessert. Yelp took me to Bar Harbor Cheesecake Company where you can order a mini “flight” of different cheesecakes — from over 30 flavors to be exact! Why don’t we have something like this in Dallas? It would be an overnight sensation. Take your family or partner here. They also offer cheesecake and wine tastings. Solo me just picked a flight of four cheesecakes to go and walked down Main street. It was a pleasant surprise to see several mom and pop shops still open and a couple of inns had fire pits on the lawn.

I ended up at my hotel around 8pm and set my alarm for 5am the next morning to try to catch the famous sunrise at Cadillac Mountain. It had been a marathon day but I couldn’t get enough of Acadia.

Day #6: Acadia to Portland, ME

I snoozed my alarm and slept in till 7:30am, obviously missing the sunrise. I guess I’m human after all. Unfazed, I typed Jordan’s Restaurant (thanks TripAdvisor) in Google Maps and headed straight for those famous wild Maine blueberry pancakes. My kind Ukrainian waitress and the senior citizen cook who paid me a compliment made this experience even sweeter. And yes, the hype is real — these were the best blueberry pancakes I’ve ever had in my life. I will drive another 5 hours to get more of these in my belly!

The post-breakfast plan was to hike at least one or two more trails in Acadia before driving south to Portland, ME. I had never been to the city and wanted to see what I would like there. As a Scorpio true to her nature, I went back to the water. Otter Cliff is just as beautiful in the early morning light. In fact, it was even better than the afternoon before with no cars or crowds. You could hear the distant bell buoy ringing out with the rocking of the waves. The light breeze rustled the balsam fir and the perfume it released made me think of Christmas. God, why can’t I just live right here?

From high up and far away I watched a pair of researchers track wildlife down below to where the rocks met the ocean. I like to imagine they were looking for mollusks and otter nests. As soon as tourists started to trickle in the area I left to visit Jesup Path and Hemlock Road, a recommendation from a photographer friend who had just been to Acadia a few days before me. This fairytale trail was one of the highlights for me. Birds were singing, leaves were falling, and the music in my earpods was syncing with everything around me.

I wanted to go to Bubble Rock but I knew I didn’t have time. In hindsight, the biggest do-over from this trip would involve me skipping Portland for another day in Acadia. It’s ok — now I know for the next visit. I stopped in Ellsworth on my way out of Bar Harbor for hot coffee and a slice of blueberry pie to go from Flexit Cafe. It rained the rest of the day towards Portland. Three hours later, I land in Old Port where I would order my second lobster roll ever at Becky’s Diner (my first choice Portland Lobster Co was closed). This was pretty good but not as good as lobster-roll-cherry-poppin’ Charlotte’s IMO.

I walked a few blocks around Old Port and stopped in a couple of shops before driving to Cape Elizabeth for the sunset. Sunsets were definitely a theme this trip. I loved the texture of the wood and stone at this coastal edge. I could see myself sitting here for hours if I had a full day. Tired and cold, I’d head back to my hotel room and unwind with my Ellsworth blueberry pie and a black and white film. Thank God for Netflix access away from home.

Day #7: Boston to Cape Cod

This is it — my last full day of my New England trip. I took off from Portland in the morning and checked in my downtown Boston hotel by lunchtime. An old Dallas coworker and friend reached out and said he and his business partner were in town too and invited me to join their day trip to Cape Cod. I had never been to Boston and had loose plans to explore the city, but I couldn’t pass up Cape Cod — too many friends already told me I should try to go. I welcomed the company and adventure. It was the perfect ending to a solo trip.

Back in the car I’d go with a professional production team. Conditions were foggy and misty, but it made for incredible photos at Kalmas Beach Park. The sun momentarily blessed us for an hour by the time we got to Nauset Lighthouse— just enough time for us to get some drone footage too.

I saw my first wild sea lion in the waters at Nauset Light Beach. We scoped for white sharks (there were signs) but didn’t see any. Yelp took us to a great waterfront restaurant called Fanizzi’s for a late lunch before we chanced a sunset at another lighthouse nearby.

When we got to Race Point Beach the sun had already disappeared and we weren’t going to get a sunset. We did however get our rental stuck in the sand and it was getting dark. Luckily for us we caught a group of Jeep enthusiasts on their way out and they helped push while I took pictures. Yay, adventure!

We took that as a sign it was time to head back to Boston. 2 hours later I was back at my hotel packing for my flight home the next morning.

The Wrap Up

To those wondering, mostly 99% of the people I came across my journey were wearing a mask: at the airport, on the plane, in restaurants, on park trails, at the harbor, and at every accommodation I stayed. Restaurants were social distancing and reservations were recommended. Massachusetts specifically has serious precautions in place for out-of-state visitors requiring them to sign travel forms claiming they have either A) taken and received a negative COVID19 test within 72 hours or B) quarantine for 14 days. A few tourist attractions and activities were closed or canceled like the famous Halloween festivities in Salem and Ben & Jerry ‘s factory tour. Regardless, there were still plenty of things to do and see — choose to be flexible in situations like these.

This is a new era of travel and socialization for everyone and we’re all learning, coping, and adapting in the best ways we can. It has become a challenge to plan for next year and the years after that with so many unknowns, but as long as you research, use the tools provided by communities and keep an optimistic and hopeful attitude, you’ll get there — one way or another. Be open to others and open to opportunities. Don’t stop exploring.



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Penny Kim

Penny Kim


Marketing Director, photographer, world travel enthusiast. Eat, think, and travel plenty.