New England Fall Foliage Road Trip

November 3, 2018

Let me preface by saying this was a beast of a trip to plan, mainly because of all of the logistics: duration of trip, being considerate of distance between destinations, finding things to see and do in each location, finding reasonable yet yummy restaurants, finding affordable accommodations in a central(ish) location- you know, the works! After 932 miles and about two and a half tanks of gas my very first Fall Foliage Road Trip was a success. Here are the details.

North Conway, New Hampshire

North Conway was the first stop on this road trip! It was perfect because not only had I always wanted to go here but it was just a quick hour and a half, scenic drive, away!

Stay: Huttopia

Bookable through, Glamping Hub,  this little tent in the woods couldn’t have been more perfect for a two night stay. It’s located just outside of Conway, in Albany New Hampshire, but it’s only a five minute drive into town.

There are two separate sleeping areas. On one side there is a full bed, separated by the fully enclosed bathroom, and on the other side there is a full bed and a bunk bed on top. It’d be cozy but you could easily fit up to 6 people in this tent! Linens and towels are provided too!

In the shared common area there is a small electric heater, kitchen and a dining table. You’ll find all of the essentials, including a sink, soap and sponge, and small refrigerator. Outside is where you’ll find the fire pit and gas stove for a little al fresco dining.


Barley & Salt

If you can manage to peel yourself away from the in room dining in your tent, head to Barley & Salt. Think home style cooking with and endless cocktail and beer list. Pro tip: order the Brussel sprouts as an app, they will not disappoint.

See & Do

This is a central location for exploring the Kancamagus Highway and lemme tell you, this is something you wont want to miss.

North Conway

There are plenty of things to do if you stay right in North Conway. From shopping to eating to taking a scenic rail ride! Whatever you choose to do, you’re sure to feel all the fall vibes.

Kancamagus Highway

Stop and pose with a White Mountain National Forest Sign and pull off in one of the countless vista points. If its hiking season, the hikes here are endless. A great resource for finding the type of hike you’re looking for is All Trails.

Mt. Washington Auto Road

Obligatory stop when you’re in the area. It’s about $40 per car to make the 8 minute drive to the summit. If it’s a clear day, I highly recommend making the drive- if only to get the “This car made it up Mount Washington”  bumper sticker.

Artist Bluff Trail

This is in Franconia Notch State Park and if you’re doing all of the above in one day, I’d reserve this for either first or last. This trail is about a 1.4 mile loop and is heavily trafficked. I would say this can be considered a beginner level hike as I saw children and elderly people hiking it! The views from the top are well worth it, too.

East Burke, Vermont

Stay: Cozy cabin in the woods

This family owned and custom built cabin is located near East Burke, Vermont in an area known for its beautiful views and mountain biking trails. It’s a little off the grid, there’s still electricity, it’s just in the middle of the woods. Cell service (I have T-Mobile and my mom has US Cellular) was real spotty and there is no Wi-Fi provided, but that’s okay for a little while. It’s always so refreshing to disconnect.

Aside from being situated on hundreds of acres, this cabin comfortably sleeps two families.

One king-size bed, one queen-size bed (in the loft), a double, and four bunks provide ample sleeping! There is also a full kitchen with a gas fridge, gas stove, and a solar-powered electrical system with a backup generator. Of course you have all the basics too like dishes, utensils, a dishwasher, an oven, basic pantry items, a refrigerator, and a commercial style stove. There is one bathroom with a double shower and huge tub. No literally I had to climb over the edge of it to get in.

For entertainment, there is a small television (for playing DVDs only) and an AMAZING stereo with aux input, games, and toys. The stereo might have been my favorite part. It played throughout the entire cabin which I loved.

We didn’t do much in this area as we were only here for a night but there is a small town with a café and grocery store about 20 minutes away if you need to pick up anything. This is really the ideal spot for big families or a large group of friends that just want to get away and enjoy each others company! 10/10 would come back to this spot with all the people I love.

Shelburne, Vermont

Stay: Hill Farm Inn

Ahhh, this sweet oasis. I have to say, after spending the first few nights in cabins/tents it was so good to be back in the comforts of a boutique luxury inn. What I love about staying at smaller inns like this in comparison to large luxury hotels is that the hospitality is individualized rather than commercialized. If that makes sense? Hill Farm Inn is a collection of individual guest room and a couple of free-standing accommodations.

I stayed in the Battenkill Suite. This is on the second  floor in the main inn building.  Also known as the honeymoon room. The four poster king bed was the main event in this room. I am such a sucker for poster beds. The bathroom is roomy with marble accents and even a tub. Have I ever mentioned I love tubs?

The restaurant offers breakfast (no lunch or dinner- you’ll need to go into town for that) and private dining options for large groups. If you have any food allergies let the staff know ahead of time and they will accommodate your needs as best as they can.

Eats (in neighboring Manchester, VT)

Shelburne is a quick 10-minute drive from Manchester which is where you’ll find all of the shopping and restaurants.

Seasons Restaurant

I loved the food options at this spot but I have to be honest, I didn’t experience the best service. It was pretty slow and sporadic but that’s okay because its not always the easiest thing finding restaurants that I can actually eat something at.


This is definitely more of a bar atmosphere than anything else but their sweet potato fries CAN GET IT! So good. I imagine, when its not off season, people head here after hours for a few drinks with friends. I can see the crowd being a mix of ages but mostly mid 20’s.

See & Do

The weather wasn’t the best when I was in the area (shocker) but there are still plenty of things to do.

Mount Equinox Skyline Drive

For about $25.00 you can make your way up 3,235 feet (the highest point in the Taconic Mountain Range) for some of the most beautiful views in the area. There are plenty of picnic spots and there is a fireplace for grilling at the first area located 1/4 mile from the entrance of the drive.

Jenne Farm Viewpoint

This is a bit of a drive but if you aren’t staying in Woodstock this is the perfect opportunity to hit two birds with one stone. Jenne Farm Viewpoint is about an hour and a half away from Hill Farm Inn and then it’s another 15 minutes to Woodstock. Both spots are quintessential fall foliage New England and should definitely not be missed if you’re in the area!

Walk around the town of Manchester

Take full advantage of being so close to this charming town when staying at Hill Farm Inn! There is plenty of shopping (hi Pendleton and Northshire Bookstore). Some are centrally located while others are a bit further out but you can definitely walk between all of them!


This is not my first rodeo in Kennebunkport but it was my first time staying at The Yachtsman Hotel and Marina!

Stay: The Yachtsman Hotel & Marina

The cutest little accommodation in the area! I loved staying here because it’s a quick 5 minute walk to the center of town and its right in a marina (which means the views are beautiful). The rooms are sunlit and spacious and every single one overlooks the marina. Each bungalow style room has its own garden terrace overlooking the Kennebunk River. My favorite part (aside from the happy hour) was how colorful the rooms were. I absolutely loved the unique patterned headboards and the stripe carpet. It’s always so hard to find ways to spice up small spaces but The Yachtsman did it right!


The Boathouse

This spot never disappoints. Its right on the water in the center of town making it a hotspot amongst tourists and locals. And for good reason, the food is absolutely delicious.

Federal Jacks 

We can definitely consider this a local spot. Within walking distance from The Yachtsman this is a good spot if you’re not looking to spend a ton of money on a decent meal. Naturally I went for the sweet chili brussel sprouts and asparagus and quinoa salad. It did not disappoint! If you’re dining elsewhere, be sure to at least stop in for a drink!

Mornings in Paris & Dock Square Coffee House

Both cafes. Both delicious. For the specialty latte and light morning bite head to Mornings in Paris. For your standard cup of joe head to Dock Square. If you’re looking to sit and relax for a few, Mornings in Paris is the larger of the two!

See & Do

Walk the town

Shop for sundries and classic New England keepsakes! One of my favorites is Daytrip Society!

Drive Ocean Avenue

Queue Yellowcard. This is such a beautiful drive along the coast. If you can take your eyes off the Atlantic take a peek at the beautiful homes that get to see this view every day!

Seek out the quintessential Maine spots

Nubble Lighthouse, Langsford Lobster and Fish House, Boat Graveyard, and watching the sunrise at Goose Rocks Beach are a few of my favorite things to do when I’m wanting to get out of the center of town! And, even though you’ll be on the ocean- the fall foliage is still in full force!

There you have it folks! My very first fall foliage road trip itinerary. There are so many spots I didn’t make it to during this week but there is always next year! And I will definitely be making my way around New England again during leaf peeping szn. Have you done a fall trip like this before? Where!? I want to see all the leaves.

PS if you made it this far, you get a gold star! Here is my Google Map of my road trip. It’s categorized and features more than what’s in this blog post. I overestimated how much I would be able to see in one week driving around New England so you bet I’ll be using this map next year!


I found your blog while googling “must see in curacao”. Curacao has been a dream of mine for over ten years now and I’m super excited to say that I’m going (98% sure) for my birthday in March. Your pictures, what you write (and your outfits!) have propelled my enthusiasm. I think you and I would be great travel partners! Also, I love your style. I’d like a few tips from you on that as well.

Aw! Thanks so much! I hope you visit in March. Truly so beautiful and its people are some of the friendliest I’ve encountered while traveling.