Vermont, New Hampshire and Maine Trip

Alex Iskold
Sep 3, 2018 · 27 min read

We just came back from one of our best family vacations yet. 8 days in New England during summer were a magical mix of nature, food, art and sight seeing. Here is what we did:

Day 1: Drive to Vermont

We drove up north, and on the way stopped at Saratoga Springs for dinner. We’ve not been there before and were pleasantly surprised by this town. We had dinner at Max London’s, which we found through Foursquare. The food was good, especially pizzas. The best one was, surprisingly, their plain Margherita.

Quick piece of trivia: Margherita pizza was named after Queen of Italy with the same name who declared that pizza should not just be a peasant food. Likely thanks to her we are all permitted to enjoy a good slice. The colors of this pizza — red for sauce, white for cheese and green for basil represent Italian flag.

Margherita pizza was named after Queen of Italy

After dinner we strolled through the main street and found Kiwlin’s — one of our favorite ice cream chains. We had the obligatory lemon sorbet with chocolate fudge.

We left Saratoga Springs, and drove up to Vermont.

Day 2: Vermont - Shelburne Museum, Shelburne Farms, Burlington

We woke up in our Airbnb, and walked outside to a beautiful view. Vermont just has this breadth, and openness to it that both draws you in, and calms you down at the same time.

We were planning to get breakfast to Dutch Mill, which I visited before, but on our way there, we saw Philo Ridge Farm. We went inside and immediately realized that we should have breakfast there instead. Everything about this place was AWESOME. Fantastic looking produce, yummy pastries, great coffee, and they even had Matcha for me!

After breakfast we headed to Shelburne Museum. This is one of the weirdest and most fun museum we’ve been to. The Museum houses objects ranging from horses from old carousels, an entire ship, an old train station, a jail, to an old pharmacy. We spent solid 2 hours exploring it, and kids had a ton of fun.

After the museum we drove to Shelburne Farms. We were pretty hungry and started with lunch. There was a cart with delicious sandwiches and salads made out of freshest local ingredients. While we ate lunch chickens and roosters ran around us. This guy in particular was fun, and a little scary.

After lunch we strolled around the farm, and checked out various local creatures. We got to see the milking of the cow, pigs rolling in the mud, chickens running around at pretty impressive speeds, and even got to pet cute baby goats.

After that we headed to a local demonstration, and video of cheese making. The process was surprisingly manual.

After the cheese we checked out local bakery. The menu looked amazing, but unfortunately most of the pastries were gone. We had to settle for cookies, which were giant, but not necessarily amazing.

We left Shelburne and drove 20 mins up north to Burlington — our final stop for the day. Burlington is a college town with a fun main street, lots of breweries and restaurants. Since none of us drinks we didn’t do any beer tasting, but instead we got some tea at Dobra Tea.

Dobra Tea turned out to be a chain, and as the name suggest, it actually originated in Poland. Dobra means good in slavic languages. We got bubble teas and where pretty underwhelmed with their quality. I had Matcha bubble tea and they didn’t use ceremonial grade Matcha, so it wasn’t really great. Despite that we had a great time chilling there, sitting cross-legged in a both. The whole experience was pretty Zen.

Later, w explored downtown Burlington, checked out local stores, and then headed to the boardwalk. The views were pretty great.

For dinner we had reservations at Pizza Verita, which as you may expect, had the Mouth of Truth right at the entrance. We wanted to get food earlier, but they couldn’t sit us because the place was absolutely packed, so we had to wait until 7PM. This Neapolitan style pizza was really delicious, and we knew why the place was so packed.

Day 3: Vermont - Ben and Jerry Factory, Bread and Puppet Museum and Theater

The next day we woke up, and packed out stuff, because we would be heading to New Hampshire in the evening. We had another breakfast at Philo Ridge Farm, and then drove up North to Ben & Jerry factory.

This was one of the most anticipated stops on our trip for the kids. The factory is magical both because it is super fun, and because there is so much love and so much amazing branding lessons here.

While kids admired the ice cream, I admired the simplicity of fonts, images, the consistency in branding, and great attention to details. Everything matters, every single pixel is thought through. Everything is user experience from toilets to walls to the store to the factory and even graveyard of flavors.

We went on the 30 minute tour, where we learned about history of the company, and got a glance at the actual ice cream production. Ben and Jerry were just two awesome dudes who wanted to create a food business that was good for the world. After a few false starts they decided to make ice cream, and the rest is history.

Ben and Jerry started as an ice cream bus that drove around Vermont and ended up an internationally known brand. The facility we visited alone produced 1.5MM to 2MM pints of ice cream per day — pretty impressive.

At the end of the tour we got generous samples of the flavor of the day, which was Cherry Garcia.

After the factory we headed up the hill to the graveyard of discontinued flavors. This place is genius, and absolutely hilarious way for Ben and Jerry to celebrate the failed flavors. Each flavor had a tombstone with a brief poem about its origin and the ultimate fate.

After the factory we headed to lunch. My original plan was to visit Prohibition Pig, which I’ve been to before, and found awesome. On a whim we decided to make a change of plans, and drive for lunch to the village of Stowe.

Stowe is a cute little place where we found a local store called Harvest Market. It was exceptionally good! We bought cheese, salami, bread, salads, and local tomatoes. Everything was really fresh and super delicious.

After Stowe we drove to our next destination for the day — Bread and Puppet Museum and Theater. This was one of the most unique and strange experience we had not just on this trip, but in general.

In a true Vermont style of weird and liberal, Bread and Puppet is a Puppet Museum and Theater, basically in the middle of nowhere. The performances happen in the open circular field, where spectators drive to, park their cars and then sit around a hill to watch the show.

We arrived early, parked and headed to the museum. Inside, we found the strangest, kind of disturbing, and at the same time coolest collection of puppets from the past. The museum was literally tiled and packed with these puppets with no free space. It was unique, and unlike anything else we’ve ever seen.

After the museum, we headed to the field to watch the show. I am not sure how many people showed up, it felt like 500, or even more. The performers pulled together a bunch of buses, and used one of them as the center of the stage. The bus had a banner on it with the name of the show — The Grasshopper Rebellion.

The entire show was a political satire, focused on mocking injustice around the world and US. It was very liberal, and very anti-Trump. The show was a rapid-fire sequence of 2–3 minute sketches, with each sketch having a quick setup, and a quick conclusion. The actors used a mix of costumes and puppets to get their points across.

The show lasted for over 1 hour, and was an experience unlike any other. After the show we got back into the car and drove to New Hampshire — our next destination. We checked-in to Mountain View Grand — a great looking resort and spa, which is listed among America’s historic hotels. We had dinner at the hotel restaurant, and unfortunately it among the worst meals of the trip. Fortunately, the view was a lot better than the food.

After dinner we walked around and explored the property. We found a mini soccer field, and kicked around the ball for a few minutes. I used to play a lot of soccer as a kid, so for me kicking around the ball is always nostalgic. We then went to a local game room, and put in good effort into air hockey and foosball before calling it a day.

Day 4: New Hampshire - Flume Gorge, Mount Cannon, Old Man of the Mountain

We got up early and drove for breakfast to a local cafe called Maia Papaya. The food there was A LOT better than in the restaurant the night before. We had home made granola, yogurt and bagels.

After breakfast we drove to Flume Gorge — our first attraction in the beautiful White Mountains of New Hampshire. The place offered pretty easy 2 mile loop, with the main gorge being the highlight. We enjoyed this beautiful hike.

For lunch we drove to Woodstock Inn and Brewery, which was highly rated on Foursquare. The food, again, was pretty mediocre and we started to wonder about New Hampshire food. Luckily though, after lunch, we found a gem of a gelato place called Aloto Gelato, in the nearby town called Lincoln. All flavors were exceptionally tasty. We even left a review and added a picture on Foursquare to make sure people know about this place.

After gelato we headed back up to White Mountains, and got on the Cannon Mountain Aerial Tramway. This 7 minute ride is filled with cheesy operator jokes, but ends at the top of gorgeous 4K+ Mount Cannon.

We had about an hour to run around the mountain top and enjoy the views. Absolutely breathtaking! We took a lot of pictures, and the kids absolutely loved it!

After the Mount Cannon, we drove two minutes to our next spot — Old Man of the Mountain Site. This is a pretty famous place, and near and dear to everyone in New Hampshire. For years, they’ve admired a “face of an old man” that winds and ice carved out of the stone. Unfortunately 15 years ago the face collapsed, and we came to the site which is now a memorial.

Nevertheless the site had both amazing views, and a clever recreation of the stone face. On a plaza, you had to find marks that corresponded to our height. Once you stood there and looked through one of the metallic pools you could magically see the Old Man of the Mountain back where it was originally.

Even more impressive was the Profile Lake. We stood still for a few minutes, inhaled the karma, and enjoyed this truly special place.

On the way back we stopped by the Littleton Food Co-op — a super market sourcing local foods. We got cheese, hummus, pickles, tomatoes and other snacks, drove back to the resort and had a picnic dinner.

Day 5: New Hampshire — Mount Willard, Mount Washington

Not surprisingly, we returned to Maia Papaya for breakfast. This time Sofia had a sandwich called Elvis which was a grilled panini with nutella, peanut butter and bananas — you could not go wrong with this.

After the breakfast we drove to Mount Willard, and spend 1 hour hiking it up. On the way up we had a lively conversation about opening a Matcha store. Kids were very into it and offered to help in various roles. It was exciting to talk about different aspects of the business with them.

The hike was at times steep, but the views at the top were worth it. Mount Willard is less than 1K feet, nothing compared to Mount Cannon, but still a lot of fun when you are on the top.

After the hike we found lunch at Flatbread in North Conway — a pizza chain where local ingredients are backed to crispy perfection. We shared a few pies — absolutely delicious.

After pizza we headed to the main attraction of the White Mountains — Mount Washington. This beauty is over 6K FT in height, a highest peak in the North East, and has been a sought after attraction for centuries.

We choose to take Mount Washington Auto Road tour instead of taking a train or driving ourselves. The train looked cool, but felt expensive at $80 per person for the round trip. We drove SUV, and decided that it might be taxing to drive it up and, especially, down. In retrospect it would have been fine, but I am glad we took a tour because we had friendly, and knowledgeable guide.

Before the drive, we put on sweaters, and pants since we knew it will be pretty cold on the top. We took scenic 30 min drive up of the Mount Washington, watching the nature around us change every 1K feet. By the time we reached the top vegetation gave in to rocks.

The top of the mountain is windy. We experienced 50 mph winds, and at times it felt like we’d be blown away. That, of course, is a baby wind for Mount Washington, which apparently held a world record at for 60+ years with winds over 230 mph.

It wasn’t easy to walk around. We explored for a bit, and rushed to hide from the wind in the gift shop, and then in the museum. The museum fee was included in the tour fee. The museum was small, but pretty interesting. The Mountain served as a major place of research into cold weather. It still is, but to a lesser extend since we are now able to simulate these sort of extreme conditions in a laboratory.

After the descend, we got back into our car, and drove for about two hours to our next destination — Portland Maine. In Portland, we stopped by Whole Foods for quick late meal. Sofia was finally was able to get her hands on a jar of Ben and Jerry most popular flavor — Half Baked.

Day 6: Maine — Portland Beaten Path Tour, Victoria Mansion, Old Port

We woke up in our beautiful Airbnb in the East End of Portland, Maine and took 15 minute walk to get breakfast at the Union. This is an awesome restaurant serving delicious local food. Kids had eggs, bacon, granola, and blueberry muffins which were overflowing with local blueberries and very delicious.

In general, we found the food in Portland, Maine to be really high quality. My only complain is that entire town does not have Matcha, so I had to settle for various kinds of ice teas — not the same.

After breakfast we went on Portland Beaten Path Tour. The guide was knowledgable, and gave us a lot of information, but the tour didn’t feel really enjoyable. Maybe it was the 90 degrees heat, or the way the information was presented, but we walked away not super impressed.

The thing we got out of the tour is that pour Portland, Maine was burned down 4 times since 1630. We also learned a few other interesting things. John Ford, the famous Hollywood director, and Portland native, started his life as John Finney. At the time, Irish folks couldn’t get far in life, and John changed his last name to English Ford. After that his career took off, and he went on to create lots of famous Westerns. Only in America, an Irish guy from Portland Maine goes on to become famous Westerns’ director in Hollywood.

The walking area of the tour was pretty constrained, we didn’t really explore much by foot. Most of the tour wasn’t about the buildings or neighborhoods, but was mostly about the history of Portland, Maine, which again seemed to boil down to — and then, the town was burned down again.

At the end of the tour, we headed to Old Port, and into a fish market, where we got a chance to hang out with some local lobsters that were still alive.

After the tour we headed for lunch to Highroller Lobster Co. This place used to be a cart, and recently settled into a store on Exchange Street. Full disclosure, I violated my vegan, and even vegetarian streak on this trip. Hey, I am not crazy :)

Highroller is a super busy, real deal type of joint where Lobster Rolls are flying high, side sauces are plentiful, fries are thin, and beer is abundant. We had Lobster Rolls, Lobster salad, Crab Roll, fries, and coleslaw — all exceptionally delicious.

After lunch we headed straight for ice cream. We figured that with the heat outside it was perfectly justified. Mount Desert Ice cream was literally a few steps away, and it was another super delicious local place. The place served ice cream with fairly esoteric flavors. My Blackberry Basil was epic, but Alice’s Lemon Poppy and Strawberry was out of this world. It is no accident that the shop was called by many the best ice cream in America. They even had a picture of Obama with their ice cream framed on the wall.

After the ice cream we headed to Victoria Mansion — a museum and a local attraction. The house was built in 1800s by a wealthy hotelier who occasionally lived there with his wife. The mansion was impressive. In each room a museum guide gave us a quick background. We thought the place was worth a visit.

Across the street from the mansion we spotted a row of fun houses.

We went back to Old Port area, and checked out local art galleries. Some where pretty fun.

For dinner we had reservations at Street & Co, one of the best restaurants in town. This was one of our best meals of the trip — incredibly delicious. We had a few salads, and then shared scallops, muscles, sea food stew, octopus and local fish. For desert we ordered a blueberry pie. The blueberries in Maine are incredibly small, but tasty. The pie was good too.

Day 7: Maine — Cape Elizabeth, Portland Headlight, Bug Light Park, Portland Art Museum, Wicked Walking Tour

Next morning while the girls where sleeping I got up and went for a short run around East Side of Portland. The East side neighborhood is cute, livable, and runs into a nice park with boardwalk along the water.

For breakfast we went to Front Room, which was highly rated on Foursquare but we didn’t find that good.

After the breakfast we drove to Cape Elizabeth, twenty minutes south of Portland. This was short but scenic drive across Maine country side. We saw beautiful houses and farms along the road. Our first stop was Two Lights State Park. We really enjoyed absolutely gorgeous views, walked around the rocks, and enjoyed the water.

Next we drove back up and stopped by for lunch at C Salt — a local gourmet market. It is hard to not fall in love with all these local places. They are unique, and absolutely delicious. We had sandwiches, hummus, and pickles.

After lunch we drove to Portland Headlight which was in the For Williams State park. Again, pictures say it all — magical, fairytale-like views of the lighthouses, rocks, and water. We spent a bunch of time walking around and enjoying the views.

Our last stop before returning to Portland was Bug Light Park where we enjoyed another beautiful light house and views of Portland.

We got back to Portland and went to The Holy Donut — a famous local donut place where creative looking donuts are made out of potatoes. Unfortunately all but 4 donuts were sold out. We ate them, and decided to also come back for breakfast the next day to give the place a proper tasting.

Our next stop was Portland Museum of Art. This is a small, but definitely mighty, unique and worthwhile museum. We started on the top floor which featured works of art dedicated to animals in nature. Awesome and creative.

Lower floor had an impressive collection of contemporary art including originals by Picasso, Gaugin, Renoir, Chirico, Magritte, and others.

After the Museum we hit the local socks shack where kids got a bunch of socks with goats, grumpy cat and other necessary things.

Our dinner reservation that evening was at David’s restaurant. We had pretty high expectations of this place as it was hyped up on both Foursquare and Trip Advisor. While it was good, we ended up liking it less than Street & Co the evening before.

The food just didn’t have as much love, or seasoning in it. The highlight the hake with rice and blueberry sauce — it was AWESOME. The hyped up open face lobster ravioli was good, but not out of this world. I had an interesting mushroom napoleon dish with peanut sauce. Again good idea, but I didn’t love the seasoning.

Our last stop for the day was 8PM Wicked Walking Tour of Portland. This was another adventure the kids were looking forward to and it didn’t disappoint. The tour itself was pretty short but the guide made it really fun. First of all, the guy instantly memorized the names of 30 people who were on the tour, and weaved everyone’s name into the story. This was impressive.

The tour itself was a series of stories about strange events, ghost appearances, and haunted houses in downtown Portland. The guide made it very fun through acting out, changing the town of voice, being scary, funny, silly and speaking in variety of accents.

Day 8: Wolf’s Neck State Park, Wolf Neck Center for Agriculture, Freeport, Eartha, Sweetser’s Apple Barrel and Orchards and Winslow Farm

On our last day in Maine we got up and started the day with a tour of local bakeries. We stopped by Two Fat Cats bakery. I thought they had some really interesting pastries, but we didn’t get anything there. Next, we went to very popular and famous Standard Baking & Co. We waited in line, and got a bunch of things — everything was super fresh and crazy good. Especially this sesame and poppy pastry.

Right after, we headed to the The Holy Donut. This time all the donuts were available and we got a sample ranging from chocolate sea salt, to blueberry and lemon. As expected — delicious.

After all these amazing pastries, we walked back to our apartment, got in the car, and drove up north to Wolf Neck State Park. This was another beautiful drive, and another beautiful place. The park itself is a mix of forest trails and views of the beautiful Casco Bay. We spent time admiring the views, while kids ran around and collected sea shells.

After the park, we drove for a few minutes to Wolf Neck Center for Agriculture — a fancy name for a local farm. The place featured all the usual suspects — cows, ducks, chickens, goats, as well as a small farm stand. We bought delicious peppers, and cherry tomatoes. Overall the place wasn’t anything special, but we had a fun experience with chickens.

Sofia had a piece of pepper with lots of seeds on top. About twenty or so local chickens were minding their business behind a small net, but when they saw the pepper they got very excited. Sofia kept moving around, and the chickens were running after her. It was clear they wanted the pepper, and were getting impatient. Finally, one of them started to try to get through the net to chase after us. Sofia decided to just give up, and threw the pepper to the chickens. Immediately, all twenty chickens rushed to tear the pepper apart like a pack of wild animals that they are. We had a good laugh.

For lunch we drove to Freeport Village Station a happening place anchored around L.L. Bean flagship store. We had food at a local place called Azure cafe, which again was rated highly on Foursquare, but was just okay. After lunch we walked around and bumped into Ben and Jerry. We had to have some.

Our next step after Freeport was Eartha, which apparently, at 43 feet, is the world’s largest rotating globe. We stopped by to check it out. It was good, but nothing special.

After the globe we drove to Sweetser’s Apple Barrel and Orchards — a fun apple store, next to the family owned orchard. This place was awesome, particularly because the owner took the time to talk to us, give us history of the place, and explain a few things. We checked out the apple sorting machine, sampled some apples, and bought some for the road.

Our last stop was the Winslow Farm, where we were planning to do blueberry picking. Unfortunately, we missed the picking window by two weeks.

We drove back to Portland, rested a bit, and went out for our final dinner. We reserved Fore Street — the best restaurant in town, owned by the same owners as Street & Co, and Standard Backing & Co. Fore Street is a special, incredibly delicious place, which practiced hospitality Danny Meyer’s style. Beautiful open kitchen, salad stations, baked breads from Standard Backing & Co downstairs, and kindness of waiters added up to a very special atmosphere.

We ordered Lobster and Scallops for main and also shared a bunch of appetizers. The food was homemade, and very tasty, although portions felt a little bit on the smaller side, given the higher prices.

We finished everything and order two deserts — cherry pastry and blueberry crumble. The crumble was incredible, definitely the best blueberry pie I’ve ever had.

Day 9: Salem

On our way back home we planned to stop by Salem, MA, which is known for its Witch Hunt back in 1692. Kids were super excited to visit the Witch Museum and experience the town.

We arrived around 11 AM and headed straight to Salem Witch Museum. The museum is a bit overrated. It consisted of two exhibits, and a gift shop. The main exhibit was a puppet-based 360 degree stage where narrator in a grim voice retold the history of Witch Hysteria that swept Salem in 1692.

The second exhibit was a general history of witches from how the witches came about to new age witches and the witches of Wizard of Oz. It was narrated by a high school student, and was informative, but too short to be satisfying. The gift shop was probably the best thing about this museum. Still kids really like it.

After the museum we strolled through Salem. The entire town is very fun and mostly everything revolves around Witches. Shops and restaurants where Witch themed, with funny names. We thought this might be a fun place to come back to for Halloween one year.

For lunch, we went to Flying Saucer Pizza Company. The food was okay, but the decor was really fun and worthy of a visit. Sci-Fi heroes of all kinds covered the walls of this place — super fun.

After lunch we headed to Witch Village, another area of Salem which hosted another Witch Museum, Wax Museum and a cemetery. This place was a lot better mainly because we had a more knowledgable, and caring guide. As we walked through a short exhibit we learned a bunch of cool things about history of witches.

Back in the days, women were not allowed to practice medicine. So pagan women where forced to use herbs to help their kids and family. They got so good at it that more and more people would come to them for help. Male doctors from the cities didn’t like that, and started campaigns to discredit and vilify them. They started spreading roomers that these women were making the deal with a devil, and were evil.

To make things more scary, and link them to devil, they created posters of the green skinned women dressed in black, and flying brooms.

The truth, as usual was rather different. These poor women would spend a lot of time in the field and didn’t wash daily — the chlorophyll would literally make their skin green. The women used a broom stick and believed that it was a symbol of fertility and jumped up and down on it, in hopes that the crops would grow bigger and better. Thats where flying on a broom stick comes from.

That was the end of our amazing trip, we got in the car and 4 hours later where home.

Alex Iskold

Written by

Father of 3 cute girls, husband to one beautiful woman. Entrepreneur, VC and Managing Director at Techstars in NYC. UX, Yoga, Running, Lots of Pushups.

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