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Recapping Our New England Roadtrip


“There’s a quality about Maine which is singular and unique, I think. It’s absolutely a world unto itself.” – Artist, Jamie Wyeth

Candy shop in downtown Kennebunkport.

There’s a certain level of FOMO you have to be comfortable with when living in New York. On any given night — or morning, or afternoon, for that matter — you could not just be doing something, but you could be doing something completely unique. The opportunities for a good time (or at least, an interesting time) are nearly innumerable, especially as you zoom out from your street, then again from your neighborhood, and then once more to go beyond your borough.

When you’re traveling here, this is ideal! You could never stop moving while you’re in the Tri-State area, and you’d be able to fill your time quite successfully. Your 5 favorite bands not playing in Manhattan anytime soon? They’re probably playing in Brooklyn at some point. Your favorite team? They may be stopping by Queens, Long Island, or East Rutherford, if not Manhattan or Brooklyn.

The best meal you’ve never had is right around the corner, a remarkable and untasted cocktail is just upstairs, and we haven’t even gotten to Broadway shows, museums, surprise/word of mouth concerts, or a pick up game at the Cage in the West Village that may end up being entertaining than UNC – Duke.

The point is, love NYC or hate it, there’s as much to do per square inch as there is any place in the world. It’s not a perfect city, but it’s certainly an interesting one. So, what happens if you zoom out even further? Well, a different type of FOMO sets in, and its the type we didn’t really want to ignore.

New England is one of the most unique and beautiful places in the country, filled with the oldest American history available to us, breathtaking landscapes and coastlines, and genuinely kind people.

We’ve been fortunate to venture into New England a few times the last few years. The FOMO that first peaked our interest in the area was validated with every lighthouse and quaint downtown we’ve seen. It’s hard to beat the Northeast in the fall, so we decided to take a bit of a “babymoon” to explore even more.

We touched on the considerations behind the trip in our newsletter, but today we wanted to focus more on the trip itself, where we stayed, what we did, and what we recommend if you decide to have your own adventure!

Hidden Pond

So, Where Did We Go?

Well, we started the trip by driving to Woodstock, Vermont. We had stayed there on our anniversary in 2020, but we wanted some more time there to explore the downtown area (especially outside of the COVID conditions of our first visit).

After two nights in Woodstock, we made our way to Kennebunkport, Maine. After two nights there, we made the trek back home!

Car Options: Rental. We love using Turo when we travel out of state, but there are no convenient options in the city, so a rental from Enterprise is our current go-to.

Travel Time: From NYC to VT is about 4.5 hours. From Woodstock to Kennebunkport was about 2.5 hours. Kennebunkport to NYC was about 4 hours.

Our cabin at Hidden Pond.

Where Did We Stay?

Woodstock Inn & Resort

I’m not sure there is a cozier place on earth than Woodstock Inn at 6pm on a cold night. Why? Because that’s when they start a fire in the largest fireplace you’ve ever seen. There’s a spa and two restaurants on property, so you can find ways to spend your time without having to go far. Then there’s the downtown, which is filled with adorable shops — you can find souvenirs if you want, but there’s also legitimately good shopping to take advantage of. There are a handful of restaurants, coffee shops, and bars within walking distance if you don’t want to venture beyond the beautiful neighborhood surrounding the Inn. If you want to take a short ride, you’ll find more foliage, rivers, antique shops, and highly rated restaurants to choose from.

Hidden Pond

Summer camp for adults? An isolated oasis? The perfect place to turn your phone off and truly relax? Hidden Pond checks all of those boxes. We stayed in a private cabin that felt secluded, quiet, and private. With a screened in deck, fireplace, and a beautiful area to relax in, the living spaces themselves are dreamy, but the campground as a whole offers a lot to do. Each morning you’re woken up with coffee and pastries delivered to your cabin, there’s an incredible restaurant on property, along with a snack/wet bar, and nightly s’mores by the campfire. Combine those things with bikes to ride around the property, heated pools, a walking garden, hiking trails, and the nearby downtown Kennebunkport, and you have a truly special experience. I can say honestly that I haven’t been this relaxed during a trip in a long time.

Downtown Woodstock.

Where Did We Eat?


Mon Vert Coffee

Farmer and the Bell

Richardson’s Tavern (on property)

Red Rooster Inn (on property)

*Honest thoughts: All in all, we weren’t overly impressed with the on-property food at Woodstock Inn. One room service meal we had was very good, but we didn’t care for the breakfast buffet or our dinner at Richardson’s. Mon Vert Coffee on the other hand is an excellent breakfast option! One regret is that we didn’t try the Simon Pearce restaurant in nearby Quechee.

Hidden Pond

Earth (on property)

The Clam Shack

Mornings in Paris

*Honest thoughts: Every meal we had here was amazing. The breakfast pastries were a nice touch, and there are plenty of utensils and plates in the cabin for you to take advantage of room service (which you can order via text). The Clam Shack was the freshest lobster roll I’ve ever had, and Mornings in Paris had excellent crepes, sandwiches, pastries, and coffee — we went twice!

One note: If you do decide to order room service, be prepared for the portions and packaging. Portions are small, and packaging is meant for you to take the food out and then put it on the dishes in the room — in other words, they don’t come with dishes, so when we ordered soup, it came in a take out container. It was delicious, but we were thrown off by it’s presentation.

Mums and pumpkins around Woodstock.

What Did We Do?


Well, for starters, we made it a point to enjoy the spa while we were there. We got massages, and afterwards they allow you 2 hours to enjoy hydrotherapy and relaxation, if you choose. From there, we spent as much time as we could sitting by the fire (which is surrounded by plush chairs and sofas that look ripped straight from my grandmother’s den) with a hot apple cider for Anna, and a bourbon for me. A mixture of shopping, antiquing, enjoying the weather, and walking around downtown filled the rest of our time in Woodstock.

Hidden Pond

The staff at Hidden Pond is awesome. When you arrive, you’re greeted with an itinerary for the week and tons of info about the grounds and surrounding area. There’s no shortage of things to do, including an on-campus gym. We chose to relax as much as possible, biked to the bonfire and S’mores one evening, and enjoyed the fireplace in our cabin as much as we could — when we don’t have one at home, enjoying a fireplace is sort of a rare treat.

We spent a good amount of time in downtown Kennebunkport, exploring a ton of fun and interesting shops, and even having some fun conversations with a few locals. We finished the trip with a ride to Walker’s Point, which is where the Bush’s compound is located. Regardless of political affiliation, it was quite the scene to take in.

I can’t say it enough, Maine is amazing. The downtown Kennebunkport area and coastline are legitimately a sight to behold and feel completely unique. Hidden Pond was exactly what we hoped for as a place to kick back and relax, and we have no doubts it would be a fun place to stay any time of year (especially in the spring)!

With a successful “baby moon” in the books, we’re back in our routines and feeling the tension in our necks that comes standard with living in the city. (I can’t lie, I kinda missed it!)

Have you ever been to New England? Planning to go soon? Let us know about your favorite Northeast Corridor experiences or upcoming autumnal trips in the comments!



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