New England is my favorite place to be in the summer time. The salty smell of the sea, the crisp veggies, and the gooey s’mores at the lake. Just the best! I usually head east much later in the summer than I did this year, but I figured I’d go a few times this season since I love it so much. Going to soak it all in!
For Memorial Day weekend, I flew into Albany, New York and headed to Killington, Vermont for two days with a day trip to Lake George/Glen Lake, New York in between. After the Green Mountain state, my parents and I jumped in the car and headed to the adorable town of Portsmouth, New Hampshire, then made our way to Boston with stops in Kittery, Maine and Newburyport, Massachusetts. Five days, five states!
This post is more like a journal of what we did and where we stayed/eat. If you’d like an in-depth Vermont guide, I have a fabulous summer guide and also a fall guide – my two favorite seasons in the east!
We started the day in Killington for coffee, then made our way to one of my favorite VT stops, Long Trail Brewing Co. for lunch and brews in Bridgewater. After lunch, we headed a few miles down the road to Woodstock for MDW sale shopping and a pop into a little Vermont cafe, Mon Vert for a chocolate chip cookie and iced coffee. I also stoped at the gorgeous Woodstock Inn for a few photos near the tulips surrounding the property. I’m dying to stay there sometime soon!
We had dinner that night at Roots The Restaurant in downtown Rutland, right near Killington. This is a newly open, bigger location than their prior spot. They have the best farm to table options in Rutland County, and a fantastic wine list. It’s always on my Vermont must-stop list.
I woke up bright and early and did Hot Pilates at TrueYoga in Rutland. They also just recently moved to a new location, and the space is stunning! So bright and fresh. I love doing their Bikram and Pilates classes whenever I’m in town.
After, we headed to Glen Lake, New York to spend the day on the water. This little lake is a slice of heaven right near Lake George and Saratoga in upstate New York, a little over an hour from Killington, Vermont. PS! They have a J. Crew Factory nearby the lake. Of course we had to make a stop. We also always stop at The Docksider for a beer lakeside.
For our second Vermont dinner, we dined at Table24 in Rutland, another favorite of mine known for their farm fresh veggies, famous fondue and rotisserie chicken.
The last morning in Vermont was the quintessential Green Mountain state morning! No stop is complete without a stroll through the farmers market in downtown Rutland, followed by breakfast at the famous Sugar and Spice.
Fueled with fresh granola and berries for our road trip, we headed to the adorable town of Portsmouth, New Hampshire, about a three hour drive away. After living in Vermont for 18 years, I couldn’t believe I hadn’t been to this little town. I immediately was wishing for a summer house here…some day 😉. Portsmouth seems to have it all — gorgeous beach front homes, or shall I say estates, local boutiques, fun bars, and great restaurants right on the water. Surrounded by the smell of the sea, and only a hop skip away from Maine (1 mile over the bridge!), makes Portsmouth a very ideal stop on a summer trip. Of course we had to drive over the bridge to make Kittery, Maine our fifth state in five days!
We stayed at the Residents Inn downtown Portsmouth which was perfect for its purpose. This inn is probably the best location when it comes to hotels, and the fresh chocolate chip cookies in the lobby, along with the spacious rooms added to the comfortable stay. If I were to come back for a couples trip, I’d love to stay at The Hotel Portsmouth, a Lark Hotels location, which also owns the hotel we stayed at in Mendocino.
We eat and drank AND shopped well in Portsmouth. We had a fun round of drinks on the water at Old Ferry Landing and Surf Restaurant, and a fantastic meal at Martingale Wharf. A must-stop for happy hour provisions is Corks & Curds, a well-stocked wine and cheese shop. I wish we had more time to check out the many breweries Portsmouth has to offer! Need to go back.
Before heading out the next morning to check out Kittery, Maine, located right over the bridge from Portsmouth, my Dad and I started the day fresh with a run along the water. After, we grabbed green juices at The Juicery, followed by french croissants and oat milk lattes at Elephantine Bakery (the cutest), then finally breakfast at Popovers — the Popover filled with scrambled eggs and cheese is a must. Thank god I went on that run. 🙂
Stopping in Newburyport, MA on the way to Boston was the best idea! I could also see myself living here…so quaint! We stopped into a few restaurants for a glass of champs and a lobster roll. Since I was really having myself quite the foodie day, we followed up lunch with an ice cream cone after stopping at a few cute boutiques in town.
We arrived in Boston by late afternoon and spent the rest of the day in Seaport, my personal favorite area of the city. We sipped Rosé at Legal Seafood’s rooftop bar, then headed to Cisco Brewers Beer Garden (Nantucket’s well-known brewery!)
We stayed at Kimpton’s Nine Zero Nine Hotel, the perfect boutique choice, then had dinner at Giacomo’s Ristorante before my insanely early flight back to the west coast. OMG! This was one of my favorite Italian spots of all time — the classic family-run checkered table place you’d expect in the North End. My Dad is still raving about it to this day. The line moves fast and it is well worth the wait!!