Guest post by karenj
Map tips: each color represents a different day. Click a marker to learn more about the spot, and click the star in the map header to save the entire map under Your Places in Google Maps.
Day 1: Getting to Hartford
We left Cleveland in the evening and arrived in Hartford around 8:30pm. It was a little over an hour drive to Kent, CT so we arrived at our B&B (The Starbuck Inn) kind of late. The owner was helpful in keeping in touch and making sure we had everything we needed once we arrived.
Day 2: Connecticut towns
- Kent Falls State Park
- New Milford
- Washington Depot
- Hopkins Vineyard
- Kingsley Tavern
The next morning we got an early start on the day! First we headed to Kent Falls State Park, and did a little hiking (and by hiking I mean climbing the nice wooden staircase that’s built by the waterfalls). It was a lovely little jaunt and the waterfalls were quite pretty.
We are huge fans of Gilmore Girls, so next we went on a little tour of CT trying to find the towns that inspired/resembled Stars Hollow. First up was New Milford, which I think was the best one! Great town to walk around – and they had a farmers market in the town square which was an added bonus. Next we went to Washington Depot, which is supposedly the main inspiration for Stars Hollow. We didn’t find it to be as pleasant to walk around as New Milford, but they did have a bookshop and some other quaint stores.
Afterwards we went to Hopkins Vineyard for some lunch and wine. I recommend this stop if you’re in the area! There’s a nice view of a lake and the wine and cheese plate were enjoyable! We also briefly drove by the Mayflower Inn and Spa (inspiration for the Independence Inn in Gilmore Girls), but it was very fancy so we literally drove into the parking lot and then drove out.
We finished the day back in Kent, which really is a perfect place to stay for this type of CT adventure. Lots of great shops and restaurants. We enjoyed our dinner at Kingsley Tavern! I should also mention the Starbuck Inn was a great place to stay – nice hosts, beautiful rooms, delicious breakfast, good location.
Day 3: Stowe
- Mark Twain House & Museum
- Ben & Jerry’s Factory
- Salon Salon
- Trapp Family Lodge
The next morning we set out for Hartford, to tour the Mark Twain House. I’m a sucker for literary/house tours, so I loved it! From there we headed to Vermont, which was a bit of a lengthy drive (over 3 hours). Our first stop in Vermont was the Ben & Jerry’s Factory. It was a zoo!! While the flavor graveyard was amusing, the factory tour itself was a bit of a snoozefest (to be fair, they weren’t producing anything that day). I would actually skip this stop if I did it all over again. We wandered around Stowe a bit afterwards to try to get some good sunset pictures (you’ll see one I snapped in the gallery – it was taking from the parking lot of Salon Salon). I would love to spend more time in Stowe if I got the chance.
This night we spent at the Trapp Family Lodge (yup, the Von Trapps from the Sound of Music own this hotel!). I really enjoyed our stay here. It was pricey, but totally worth it for the ambiance. We had dinner at the Bierhall, their own brewery on site, and they had fantastic chicken schnitzel. There was a bit of a long wait so we ended up eating at the bar.
Day 4: Vermont to New Hampshire
- Cold Hollow Cider Mill
- Morse Farm Maple Sugarworks
- Cabot Creamery Visitors Center
- Deacon Street
- Cranmore Inn Bed and Breakfast
The next morning we started out with breakfast, and then a Von Trapp Family History Tour. I really found this to be quite interesting. We learned a lot about the Von Trapps, who came to this area of Vermont after they left Austria (it reminded them of home). After a talk from our tour guide and a tour of the cemetery, we were taken into the hotel to watch a video and hear directly from one of the Von Trapp’s grandchildren. So interesting and engaging.
When we left Stowe a little after noon, we made a couple of quick quintessential VT stops: Cold Hollow Cider Mill (to buy cider donuts) and Morse Farm Maple Sugarworks (to taste some maple syrup). Cold Hollow Cider Mill was CRAZY busy so we didn’t stay long, but the donuts were top-notch. I enjoyed Morse Farm more. Nice videos, enjoyable paths to walk, and a good store. You must get a creemie (maple ice cream). I wanted to stop at the Green Mountain Coffee visitors center/café, but no time unfortunately. We did also briefly stop at the Cabot Cheese Visitors Center, which was okay as well. Sampling their cheese options made it a pretty cool stop – not a necessity to visit, but a good stop on our way to New Hampshire.
It was about a 2.5 hour drive from VT to NH, and it was pouring rain the whole way, so not the best drive of the trip. Once in NH we dropped our stuff at the Cranmore Inn, our home base, and headed to dinner at the Deacon Street Restaurant and Martini Bar. Good food, but weird atmosphere. Just kind of “meh.”
Day 5: North Conway
- Conway Scenic Railroad
This day didn’t require any driving! We took the Conway Scenic Railroad 5-hour ride. It was very nice! We sprung for seats in the dome car, but to be honest it wasn’t worth it. We spent most of the time in the open-air back of the train so that I could take pictures. If I did it over again I’d be buy cheap indoor seats (in case the weather was bad) but then hang out in the back most of the time. It was a very pretty train ride though, and I would recommend it if it in the area. Visually stunning. Dinner was quite unremarkable at Horsefeathers. Wouldn’t recommend it. We did a bit of shopping in the area, and then crashed at the hotel. We paid for a cheap/small room at the Cranmore Inn, but it was adequate.
Day 6: Mount Washington
- Mount Washington Auto Road
- Archer’s on the Pier
- Rockland Breakwater Lighthouse
- Acadia Hotel
When we left North Conway, we headed to the Mount Washington Auto Road. We didn’t feel like making the drive up ourselves, so we did a guided van tour. Totally worth every penny! We still got to enjoy the ride up, but both my husband and I could pay attention to the lovely scenery. You can also take a cog-wheel train up the mountain, which looked cool, but I liked the Auto Road. Once on top, the views were breathtaking! I loved getting our picture taken at the summit, where they have the “coldest weather in the world.”
After our tour, we hit the road for Maine. It was about a 3-hour drive. Our first stop was Rockland, where we had lunch at Archer’s on the Pier. I had a phenomenal lobster roll and blueberry pie. We then drove over to see the Rockland Breakwater Lighthouse. This was a great stop! If we had more time we might have walked all the way out to the lighthouse, but it was getting dark and we were afraid we wouldn’t make it back.
From Rockland we headed to Bar Harbor, our home base for the next 3 days. We stayed at the Acadia Hotel, which was awesome! Fabulous location. We weren’t terribly hungry when we got there, so we had drinks at the Irish Pub next door. They had a fantastic blueberry mule, made with blueberry jam.
Day 7: Bar Harbor
- Cafe This Way
- Thunder Hole
- Jordan Pond
- Cadillac Mountain
- Abbe Museum
- The Independent Cafe
The restaurant Cafe this Way was next door to our hotel and was a great place for breakfast – get there early!! Breakfast was included at the hotel, but it was more of a continental breakfast which is why we went to a restaurant.
We did a guided 4-hour trolley tour of Acadia National Park this morning and visited Thunder Hole, Jordan Pond, and Cadillac Mountain. It was a good orientation tour, even though we went back to some of those places on our own the next day.
We also visited the Abbe Museum, which was a nice stop and a good museum, even if for a quick visit. Oh, and you must stop at the Independent Coffee Shop to get a “Jean Acadia.” The best coffee/ice cream drink ever. Trust me! We loved our dinner at Galyn’s! Great view! Great lobster! Great blueberry cobbler! I really loved the walk-ability of Bar Harbor and it was my favorite stop of the whole trip. Highly recommend to anyone thinking of a unique place to vacation.
Day 8: Acadia National Park
- Carriage Road
- Stewman’s Lobster Pound
We did some hiking the next morning which was a bit of an undertaking for two non-hikers. We wanted to see some of the Rockefeller bridges, so we walked the carriage roads, and then hiked around Jordan Pond. It was an adventure. We had lunch at Jordan Pond Restaurant to get some popovers – a very touristy stop, but worth it. We did some shopping around Bar Harbor the rest of the day, and just enjoyed the town! Dinner at Stewman’s Lobster Pound was fine, but not super memorable.
Day 9: Portland
- Penobscot Narrows Observatory
- Maine Duck Tours
- Portland Head Lighthouse
- Elsmere BBQ & Wood Grill
When we left Bar Harbor we were headed for Portland. We made a brief stop at the Penobscot Narrows Bridge and went to the top of the Observatory. Nothing to write home about. We almost got stuck behind a bus of tourists, and thank goodness we didn’t – only a couple of small elevators to the top. It was nice viewing the bridge from afar, but I wouldn’t ride to the top again. When we got to Portland we grabbed lunch, and then went on the Downeast Duck Tour. BLAH! Did not enjoy. Would have preferred to spend time on our own in Portland. We walked around a bit after the tour, and then headed to the Portland Head Lighthouse. We spent hours here. I LOVED it. So beautiful, and we were there right before sunset so the scenery was perfect for picture-taking. We went to a place called Elsmere BBQ & Wood Grill for dinner and it was nice to have some Mexican food among all the seafood! We stayed at a VRBO for the night, which was a nice change of pace.
Day 10: Kennebunkport
- The Cookie Jar
- Wedding Cake House
- Dock Square
Day 10 was a bit of a mess. We went to the Cookie Jar bakery near our VRBO to grab some breakfast, which was a good start – delicious pastries. Next we went to Kennebunkport, which was a gorgeous place to walk around, and I would recommend a stop here. We drove by the Wedding Cake House, and spent some time in Dock Square.
But then we headed to Salem, MA. There was some type of motorcycle rally and we never actually found a parking spot. We drove around forever, and it looked like a cute town, but we never got out of the car. Made a note to come back in the future! We managed to find a restaurant just outside of town to grab one last lobster roll, and then drove the 2 hours to Hartford. We spent the night near the airport as we had an early flight the next morning.
Traveled in October 2017