My First Solo(ish) Vacation!

Hi friends!  It’s been a day, give or take 80, since I last posted.  I know, I know, I always promise to be better about writing more frequently, but to be honest the last thing I wanted do after a long day at work was come home & look at a computer screen again.  I’m sure many of you can relate.

However, in the last few months a lot has changed.  Yes, I’m still boycotting The Bachelor, so no recaps.  Yes, I’m still watching Hallmark movies, but I thought the 2019 Christmas ones were terrible, except for Christmas at the Plaza.  But, I did watch 90% of them.  I also watched many of the Lifetime Christmas movies, and maybe I liked them better?  There was more diversity, the female lead was allowed to have straight hair, they typically got to the kiss much earlier in the movie, & I saw alcohol.

The biggest news of all though, is that I got a new job!  It happened very quickly & unexpectedly, but now I work from home!  Y’all, I’m saving 1.5 hours of drive time.  I also haven’t filled my gas tank in 14 days!  This is a miracle in & of itself.

Anyway, I felt it was high time I got on here & wrote about my 8 day trip to Connecticut, Cape Cod, & Nantucket last September.  The first five days of the trip were solo, then my friend Katy joined me in Nantucket.

Y’all are going to laugh at me & think I’m a super nerd, but my favorite show of all time is Gilmore Girls.  With that said, the first three days of this trip was me road tripping around Connecticut to all the little towns that inspired Stars Hollow.  Could there be a cuter name for a town?

Okay, grab a cup of coffee (Dunkin’ in you’re in the northeast) & settle in…

This was my itinerary: 0C07418B-8980-4734-A64D-B0AAA4813D7C_1_201_a

The way I like to plan trips is to create a calendar with the dates I plan to travel.  Then I like to research what’s happening in the places I want to visit & just write down anything that looks interesting, including restaurants, shopping, museums, etc.  This also allows for you to purposefully avoid certain things and to budget accordingly.  For example, while I was in Nantucket there was a Gilmore Girls Fan Fest in CT, so I purposely avoided Connecticut during that weekend & did my personal GG tour the weekend before.  As much as I love GG, I’m not into herds of people.  Once I see what’s going on then I layout the order of towns I want to go to & book hotels accordingly.  I filter out activities once I’m there in the moment.  Oh, in New England I try to stay at B&B’s or inns exclusively.

Saturday, September 21:

I departed Houston bright & early and arrived in Boston by lunch time.  I hopped in my rental car & purposefully took the scenic route from Boston to Litchfield, CT.  A note for the rest of this post, I always choose the scenic route & plan for longer drive times.  The drive from Farmington to Litchfield, specifically, is a must do!  Y’all, I’d move to Farmington or Litchfield tomorrow if I thought I could make a sustainable living.  So cute!

I stayed at the Litchfield Inn, which is supposedly what the Independence Inn (GG) was based on.  I totally see it.D0FBF113-2B53-420A-951D-EAD17917046C

If I’m being completely honest, I probably would not stay here again.  The staff was lovely, but the building was very old & had original walls with little to no sound proofing…and there was a very raucous wedding reception going on until close to midnight.  Call me old fashioned, or just call me old, but I was tired & couldn’t sleep due to the loud music and wedding guests running through the halls.  Had I known about the wedding before hand, I would have stayed somewhere else.

On a funny note, the room decor was wild…or wildly bright! Reds, teals, faux brick, wood paneling, wall paper – you name it, this room had it.

That night I had dinner at a cute (but packed!) restaurant down on the main street, called At The Corner.  You guessed it, it was on the corner!  Litchfield doesn’t have a town square, at least not that I saw, but it had a street that most shops & restaurants were on.  I sat at the bar & made friends with my neighbors (Tom & Lori), while enjoying a beer flight of IPAs (I let the bartender choose) & enjoyed the primadonna salad.  Picture Tom as Fred Armisen & George Clooney’s love child, & picture Lori as Sarah Jessica Parker.

Sunday, September 22:

I woke up early & headed to breakfast at some diner Tom (from the night before) recommended.  Didn’t take pictures, nor was the biscuits & gravy any good.

Moving it along, I quickly got on the road to Kent, CT to see the Cornwall Inn – it was also supposed to have inspired the Independence Inn.  I didn’t see the resemblance.  This town was super cute, but since it was a Sunday nothing much was open, except for a coffee shop.   Whomp, whomp.

I will say this entire route was very scenic even though I was on a highway, albeit a 2 lane highway.  The leaves were just starting to turn for “Leaf Peepin’ Season.”  Can we rethink this name?  Another funny thing I noticed was the complete lack of cohesiveness in terms of how close the houses were to the road…which again was a 2 lane highway.  Some houses were literally on the edge of the road, their neighbor was maybe an olympic swimming pool length away from the road, & the next neighbor was maybe a car length away from the road.  Half way through the day, it finally (FINALLY!) dawned on me that the houses were most likely there before the road was, you know because they were built in 1723 or something.

I quickly headed to New Milford, CT, which was where “Luke’s Diner’ & the town gazebo were.  This town was freakin’ adorable.  Lots of churches.  I didn’t think the gazebo really  looked like GG, so didn’t get a pic.  Theo’s Diner (aka Luke’s) had a great BLT.  Across from Theo’s was a little art gallery in the old train station, how cute is that.  The proprietors told me that there was an awesome flea market in town (maybe called The White Elephant?), but I didn’t have time to stop by.

Movin’ on down the road, my next stop was Washington, CT, some call it Washington Depot – I’ve seen it called both.  This was THEE inspiration.  Here I found Doose’s (aka Washington Food Market), the Dragonfly Inn (aka Mayflower Inn), & the church (aka Town Hall).  I saw so much of Stars Hollow in this town, & I loved every bit of it.  Word to the wise, if you blink you miss this town.

On my way to the next town, Guilford, CT, I had to pull over for a firetruck.  And, low & behold look what I stopped in front of. A6E7D613-B558-4BA3-8F7E-10191FD966F3

Stars Hollow High – said in the monotone of those same 3 kids for every Stars Hollow production.

Unfortunately, I arrived in Guilford near closing time, but I did manage to stop by The Village Chocolatier, a book store, & a spice shop.  This town was super cute, & had a proper town square.

Rounding out the day, I stopped in Mystic, CT for the night.  Mystic has nothing to do with GG, but I didn’t get to spend much time here on my last girl’s trip with Jessica & Brigitte so I made a point to come back.

I stayed at the Whaler’s Inn, which is the perfect place to stay.  It’s in the middle of town and you can walk everywhere.  They also just completed a renovation, but don’t worry it is still charming, historic, & has sound proofing!

I had dinner at the Engine Room, & their hush puppies are to die for.  Seriously, I still think about them…

Monday, September 23:

The next morning, I ate breakfast at Grass & Bone with the voucher I got at checkin at The Whaler’s Inn.  My breakfast taco was tiny, but delicious. 6CE68131-A447-46FC-AE22-21F9B9F080D7

After breakfast I spent a leisurely morning going in & out of shops all over town.  It was quite nice after the pace of Sunday.  Mystic has a great bookstore (think it was called Banks Square Books) & I’m kinda kicking myself for not buying anything there…does this mean I need another trip?

By lunch time I was on the road to Cape Cod!  I have been dying to go to the Cape (do I sound like a local?) for years.  Cape Cod is divided into several areas, Upper Cape, Lower Cape, Outer Cape, Mid Cape, & probably some other Capes too.  I stayed in Mid Cape so that everything I wanted to do wouldn’t be more than 20-30 minutes away.

Before checking in to my inn, I stopped in Sandwich first.  I went to the Green Briar Jam Kitchen to pickup some jams for Mama J; some TSA agent got to enjoy those in Boston instead.

Next I headed to the Sandwich Glass Museum.  I loved it!  I got to watch glass being blown, a short film about the history of the town of Sandwich, & lots of dioramas!  I love a good diorama.

I chose to stay at the Winstead Inn in Harwich, MA.  It was a good choice because it was centrally located to everything I wanted to do.  My room had a little kitchenette, which came in handy because by this point I was kinda tired of eating out by myself.

The Winstead had a great breakfast, & I highly recommend this place.  The staff was fantastic.

On a side note, isn’t it so pretty how the bright summer hydrangeas fade to these beautiful fall colors? C071AB92-97B2-4837-9685-40DF54567317

Tuesday, September 24:

This was my day to explore the Lower & Outer Capes.  My first stop was the Atwood House Museum, which turned out to be a total bust.  The museum hours had changed due to Daylight Savings Time.  I made the best of the situation and drove around Chatham for a bit.  When you close your eyes & picture your idea of Cape Cod – you are picturing Chatham.  It is quintessential Cape Cod, not to mention a very picturesque fall.

Side note, when I saw this lighthouse I could not stop singing “Candle on the Water” from Pete’s Dragon.  I’m pretty sure I sang that song in choir at some point because I new all the words.

This little jaunt gave me several questions, maybe you can answer them.  None of the locals satisfied my curiosity.

  1. Why do people name their houses, where do the names come from?  Is it a seafarer’s house, or a captain?
  2. What is with the pumpkins above the doors?  So many houses had this, & I think is a really cute, but dangerous?
  3. So many houses had the shingles on one side of the house & then siding on the other sides.  Is this an aesthetic thing?  Is it a money saving thing?  Does it have to do with wind coming off the ocean?  WHY? CA3BE3C4-768D-4BC6-8F4D-44520DE9592F

Next up on my agenda was wine tasting at Truro Vineyards.  It was super fun; however, all the wines were too sweet for my taste.  The experience was really fun though & you should go there.  Tastings were $10 for six wines.

After wine tasting I headed down to Provincetown (aka P-town).  Y’all, I know everyone loves Provincetown, but the parking situation ruined my P-town experience.  Also, if you’ve ever been to Venice Beach in LA, then you’ve been to Provincetown.  There.  I said it.

Wednesday, September 25:

I stuck to Mid Cape & the Brewster area.  This was the best day ever because I found Dr Pepper at the Brewster General Store!!!  I heard angels singing in that store.  Haha.  This store was so cute.  Old men come every morning & sit on the benches out front to “shoot the breeze.”

Look at those corbels!  So dreamy.

While in Brewster, you should stop by the Lemon Tree Village for some shopping.

I somehow landed at the Edward Gorey House Museum.  Y’all, do not sleep on this museum.  It’s weird, quirky, & delightful.  For those, like me, who don’t know who Edward Gorey is – he was an illustrator most well known for Dracula.  Seriously, check out his Wikipedia page.  We had a character of a museum guide, he was perfect for the quirkiness of Edward himself.

I made a quick stop at the Cape Cod Chip Factory – they are my favorite.  This place will take you 10 minutes tops to go through. 26127154-3F08-4355-B6B0-968D782E3670

Around the corner, I stopped by Cape Cod Beer, for my beer flight.  Unsurprisingly, I liked the IPAs.

A few final thoughts about Cape Cod…  I would love to spend an entire summer there & really immerse myself & get to know all the little towns.  It didn’t look like I thought it would, meaning that I thought it would be more “beachy.”  There was so much forest, I was truly shocked.  Good for MA for preserving land like that.  Also, if you love old cemeteries (I think they are pretty), then you will love the Cape…all of New England really.

Thursday, September 26:

Off to Hyannis, I went to meet my friend Katy at the Steamship Authority to catch the ferry to Nantucket!  Funny story, we both had rental cars to drop off at the Barnstable Airport in Hyannis so we took an Uber from the airport to the ferry.  Our Uber driver dropped us off at Hy-Line Cruises, not Steamship Authority.  Luckily the guys taking luggage let us know we were at the wrong place.  We had to hoof it over to the Steamship dragging our luggage through the gravel paths.  Guess we got an unintentional workout in.

A note about ferry options.  The Steamship Authority cost $69 round trip and had ferries every 3-ish hours.  The Hy-Line Cruise was $77 round trip & had ferries every 1.5 – 2 hours.  It just so happened that the Steamship times worked better for what we wanted to do, & was $8 dollars cheaper.

On the island, ACK as the locals call it (also the airport code), we stayed at the CUTEST hotel.  76 Main was historic, beautiful, & classy AF.  Our room was the size of a postage stamp, but we were hardly ever there.

The great thing about 76 Main, is that you can walk to pretty much anywhere in town.  However, beware of the huge cobblestones…we had trouble in flats.

We quickly dropped our stuff off in our room & headed to lunch at Lemon Press.  Y’all we ordered a bottle of wine & it was a half bottle…we got duped.  Lunch was delicious though and the decor was lovely.

After lunch we decided to check out the Whaling Museum, cost is $20.  More dioramas! Then we got ice cream at Juice Bar (no lines in September!) & continued to walk around town.  Below are some of my favorite architectural details.

76 Main provides all the fixings for happy hour aside from the alcohol; with this in mind, Katy & I stopped at the liquor store to get wine.  Back at the hotel, we drank our wine & made friends with the other guests.  We socialized until about midnight with a couple of pilots that Katy kept referring to as the guys from Wings.  HAHAHA.  We basically drank our dinner & ate some popcorn.  Y’all we thought this was the best popcorn we’d ever had…could’ve been the booze talkin’ though.

Friday, September 27:

We got up bright & early & headed to breakfast at Black Eyed Susan, where my step sisters Amanda & Samm met us for the day!  They deserve all the accolades because they woke up at some ungodly hour & drove from Leominster, MA to catch the first ferry to Nantucket.  Black Eyed Susan is teeny tiny, you have to wait outside on the sidewalk for a table to open up.  There is literally only room for the tables inside.  After breakfast we had some time to kill before the shuttle could take us to Cisco Brewers, so we walked down the street to Hospital Thrift Shop.  Y’all, I got two paintings for a dollar.  They are hanging up in my office now.  I believe all the proceeds go to the local hospital.

We caught the 11am shuttle to Cisco Brewers & basically camped out there the rest of the day.  This is the trifecta of places to go because it is Cisco Brewery, Triple Eight Distillery, & Nantucket Vineyard all in one.  They have food trucks, people bring their dogs, there is live music – fun to be had all around.  We took the tour & got to try a little of everything before we settled in for wine flights.

We rounded out the day at Brotherhood of Thieves for dinner before Amanda & Samm had to catch the last ferry home.  I think they were awake for 21-ish hours.  Bless it.

Saturday, September 28:

We basically raced to the ferry & raced back to Boston to catch our flight home.  I was home by 6pm, & had all of Sunday to decompress.

I think the next time I go to Nantucket, because I will be back, I would stay 2+ days longer.

That’s all she wrote, folks!  It was a great trip!

Let me know where you think I should go next…

Kiss Hug,

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