Vermont and Salem, MA 2019

~ 4 Year Anniversary Trip ~

In honor of our upcoming trip to Salem, MA and Vermont for our five year anniversary, we thought we would finally share our fantastic experiences from last year! With less than two days left before we are back on the road and headed on our epic adventure, we can barely contain our excitement.

For years Russ has been telling me I would love Vermont since he had been before and knew how beautiful and relaxing it was. So, for our four year anniversary we finally decided to go for a romantic week away in the mountains after a couple of days in Salem, Massachusetts for Halloween since I had been wanting to go since I was in middle school.

We left our house after a night of next to no sleep at 4:00am and set our route to our hotel in Danvers, MA. It was an exhausting drive, but so worth it! When we finally made it into Vermont, we pulled off at an overlook by a small country store to stretch our legs and take in the beautiful fall view. It was like breathing in a deep breath of fresh air when we got out of the car and took in our first real view of Vermont.

The guardrail along the road was covered in all sorts of bumper stickers from various travelers passing through. That was when we decided to make our own bumper sticker to leave behind to mark where we’ve traveled.

After taking in the sites and stretching our legs for a few minutes, we went inside the country store to browse around for a few minutes before jumping back on the road and finishing the last leg of our trip into Danvers. While browsing the store, we did a tasting of some of Metcalfe Distillery’s spirits and wound up bringing home bottles of their maple liquor, raspberry liquor, and bourbon. Luck was on our side and a local news station was doing a segment on Metcalfe and so we wound up being filmed making our purchases!

~ Salem ~

Salem Witch House

We finally made it to our hotel around 5:15pm, and it couldn’t have come soon enough since we were absolutely exhausted after a 13 hour road trip on next to no sleep. It was rainy, so we parked by the entrance and made our way inside where we were immediately greeted by the very friendly hotel staff who promptly checked us in and handed us a warm chocolate chip cookie, water, and an invitation to the exclusive Halloween cocktail hour event that was being held shortly after our arrival exclusively for Diamond members. These are only some of the perks to being a Hilton Honors Diamond Member.

Executive Lounge Party

After completing our check in, we parked our car and brought our stuff to our room before collapsing on the bed for a few minutes before joining the party in the Executive Lounge for some light appetizers and cocktails before venturing into Salem for dinner. The Executive Lounge was full of fellow guests, most of whom were traveling for business. There were hot appetizers and various food and sweets as well as an open bar. The large windows overlooked some of the city below.

We mingled for a while and enjoyed some light appetizers and cocktails before heading to our car and driving into Salem for a delicious dinner at Brodie’s Seaport. It was raining and foggy as we parked on the side of the road across from Brodie’s Seaport. The excitement and magic of Salem pulsed around us as we scurried across the empty street and entered the restaurant.

The restaurant was warm and inviting and the staff was very friendly. We started off by getting some delicious cocktails while perusing the menu for our meal. I got the Carmel apple sangria followed by a pumpkin martini, while Russ got a maple old fashioned. All three cocktails were very good and festive.

For dinner, I got the scallops plate and Russ, of course, got an order of buffalo wings. Both of our dinners were delicious and we left feeling very full and satisfied. It was still rainy and foggy out when we walked to our car, arm in arm, and as we were about to drive away there was a man and a woman dressed in period clothes walking down the street. It was so eerie watching them disappear into the fog of the dreary Salem night.

A few minutes later, we were back at our hotel and collapsed into bed, ready for some much needed sleep before our adventure packed day in Salem for Halloween. We woke up early on Halloween and grabbed some of the breakfast included with our Diamond Membership. After breakfast, we grabbed our stuff and headed to the train station in Danvers to catch a ride into the heart of Salem since the streets were closed off for Halloween.

The plan was to wear our Hogwarts robes from our trip to Harry Potter World the year before, but since it was still drizzling we didn’t dress up like planned. We eagerly set off in the direction of the crowds, swarming the center of Salem like a swarm of bees.

The very air felt alive with the excitement of Salem pulsing through it. There were all sorts of different costumes roaming the streets. We went into several shops and bought some souvenir shirts before walking through the outskirts of town and taking in some of Salem away from the hype of downtown Salem.

After taking in everything Salem had to offer for several hours, we made our way to Lobstah on a Roll for lunch. I had been so psyched to get my very first lobster roll from here, but unfortunately we were both incredibly disappointed. The lobster tasted off and it was definitely not worth the money spent on it. The only redeeming factor was that the ice cream shop inside of Lobstah on a Roll had some delicious ice cream and the girl gave it to me for free. So, despite being recently lactose intolerant, I enjoyed some delicious ice cream as we ventured back out onto the streets of Salem.

As the sun began to set, we made our way back to the hear of Salem in time for our walking ghost tour of Salem with Black Cat Tours. Our tour guide was absolutely fantastic and brought so much energy and history to the tour. Our tour took us through the streets of Salem at night, shedding light onto the history and hauntings of Salem. Our tour guide was very animated and theatrical and made the tour so much fun. The tour ended at the memorials to the victims of the Salem Witch Trials. We both highly recommend Black Cat Tours if you’re ever in Salem and looking for a fantastic ghost tour!

After the tour, we made our way across town to Far From the Tree Cider. When planning our trip over the summer, Far From the Tree was one of the top places that popped up and peaked our interest with their unique flavored ciders. Our favorite wind up being their seasonal Apple of my Chai. We bought a four pack to bring home with us to savor the deliciousness of the unique cider that brought some of our favorite flavors of chai tea into a beverage that we already loved.

After some glasses and flights, we left feeling satisfied and made our way to the train station to wait in an enormous line to hitch our ride back to the station in Danvers so we could grab some late dinner and hit the road for our 3.5 hour drive to Smuggler’s Notch in Vermont the enjoy the remainder of our anniversary vacation!


Our drive to Smuggler’s Notch was eventful as the rain that had started as a light drizzle in Salem grew, having flooded out almost all of the roads we needed to take to get to our resort. We were coming up on the Notch pass at around 3:00am when we saw a lot of tree debris on the road and flashing emergency vehicles in front of us. The road had been flooded out and we had to turn around and try several different routes before we were finally able to make it to the resort and check in to our amazing three bedroom condo at Kestrel Woods.

We were in love with our mountain retreat that we would call home for the next week and eagerly settled in for some much needed sleep. Our condo was equipped with a entryway and a long haul that brought us to a fully equipped kitchen with a dinning area, family room with an electric fireplace and a door to a screened in porch, another hall leading to two other bedrooms, a bathroom, and the washer and dryer, and finally the master bedroom to the side of the kitchen. The master bedroom was perfect with an electric fireplace, a screen door that led us to a porch that led out to the grounds of Smuggler’s Notch, and a large bathroom with a soaker tub and a shower with a steamer. The steamer and the soaker tub were some of our favorite features along with the fireplaces!

The next day was our four year anniversary, so we woke up and get dressed in our best so that we could tour what would become our newest favorite winery, Boyden Valley Winery, and grab some dinner. Unfortunately, the weather had other plans since the flooding only got worse and flooded out both roads at the base of the mountain, so we planned our anniversary outing for another day and drove up the notch road to go exploring some. The mountains were absolutely stunning, and despite it being freezing, we enjoyed some light hiking by the Smuggler’s Notch Cave.

After we half froze, we headed back to the resort to grab some dinner at the Morse Mountain Grille, which turned out to be one of our favorite restaurants. Our server, like everyone we met in Vermont, was incredibly friendly. We had a great view of the Smuggler Notch mountain and were near a fireplace. We had some absolutely delicious cocktails alongside our delicious dinner. For appetizers, we got chili – mine was in a delicious bread boule! For our entrees, I got a pub steak and Russ got the buffalo chicken tenders. Both of our meals were absolutely delicious! For dessert we split a scoop of vanilla ice cream topped with some delicious maple syrup – a very yummy and unexpected treat.

After dinner, we headed back to our condo to open presents and relax in front of the fireplace. The next day we explored the resort some more and bought some of our favorite souvenir light up Christmas hats from the Smuggler Notch Country Store before grabbing a light lunch of nachos and warm cocktails from the Morse Mountain Grille. A little later, we headed to the country store down the street to stock up on some groceries.

Our next several days were spent exploring the resort, Jeffersonville, Stowe, and Waterbury. While heading into Waterbury to check out Cold Hollow Cider Mill, the Cabot Annex Store, and Ben & Jerry’s, we ran into some snow while crossing the mountain. We both love snow, so it was exciting and added to the magic of Vermont and was a good chance to test out my new RAV4’s AWD features.

We had some delicious cider at Cold Hollow followed by getting some apple cider donuts that were fresh out of the fryer and so very delicious! Afterward, we stopped off at the Cabot Annex Store in Waterbury and sampled all of their cheeses before buying a bunch to bring home before heading to Ben & Jerry’s for a tour and some ice cream! While in college, I had the opportunity to meet Jerry at a convocation dinner, so I was extra excited to see the facility where all of the magic was created.

After we got home, we made some delicious steaks we bought from the country store and enjoyed a nice evening in front of the fire. On the 4th, we headed into Burlington to tour the Magic Hat Brewery, a must go for Russ since he loved it the last time he was in Vermont. This time for dinner, we headed to Martell’s at the Red Fox, just down the road from Smuggler’s Notch. Russ of course got the wings and I got some spinach and artichoke dip for our appetizers and we both got their specialty burger topped with pulled pork and coleslaw. It was good, but very messy. The flavor combinations of the pork and beef was on point. It was definitely a very unique burger that we both highly recommend. Our appetizers though weren’t anything special.

The next two days were just spent relaxing at the resort and exploring. We finally made it over to Boyden Valley Winery on the 7th, just in time for some more snow flurries to start. The staff was so friendly and gave us an amazing tasting before we ordered a cheese board and some glasses of wine and a Vermont Ice Maple Creme Milkshake. We enjoyed our drinks and cheese in their tasting room while discussing becoming VIP members, which we wound up doing and haven’t regretted since and we even plan to continue our membership this year!

We left the winery with our case of wine and headed out on a snowy driving adventure to explore Jeffersonville and take in more of the beautiful sites of Vermont. On our way back to the resort, we found a road that took is through a covered bridge, so we can officially cross that off our bucket list!

Afterward, we explored the snow covered resort one last time before checking out and heading to Waterbury for our final night in Vermont before heading home. We checked into The Old Stage Coach Inn before heading to dinner at The Matterhorn. We loved the atmosphere at The Matterhorn since it was relaxed while also still nicer and with a stellar view since it was right next to a snow covered river. We ordered our cocktails and some appetizers of sushi and, shocker, wings. For dinner we got steak.

The inn we stayed at was so homey and welcoming. Our room had a four poster bed that was very comfy and definitely made us not want to wake up the next morning for our final breakfast before hitting the road back home. We headed downstairs to the breakfast room and grabbed a corner table with a great view of the snow covered grounds. Our breakfast was absolutely amazing and comprised of fresh, homemade jalapeño hot sauce that accompanied my smoked salmon eggs Benedict and the absolute best ham and cheese omelette we have ever had.

On our way out of Vermont, we made a final stop at Cold Hollow to grab some apple cider donuts and a gallon jug of apple cider to bring home with us before heading into the snow and toward home. It was bitter sweet getting home since the magic and peace of Vermont called to us, but it also felt nice to sleep in our own bed. Ever since we got home, we have looked forward to going back and so we are very excited for this year’s trip to escape the craziness of 2020 and celebrate five years together.

Happy travels!

Lindsey and Russ


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