My New Favorite Place to Watch the Kentucky Derby

Yes, I think I found my new favorite place to watch the Kentucky Derby!  In the past, we have attended Kentucky Derby parties in our neighborhood or watched the race from local restaurants.  Usually, we just watch at home with the kids.  Basically, the four of us pick a few horses and cheer them on while our dog, Rosie jumps up and down, trying to get in on the action…yeah, exciting stuff.

This year, Derby Day fell on the same weekend as my girl’s getaway.  For once, it was exciting to make a bigger deal out of the event – especially since our hotel was hosting a Kentucky Derby Party!

Hotel Derby Party…

For this girls’ getaway, we traveled to the beautiful island of Martha’s Vineyard, Massachusetts.  I will include a link to my full trip report below but for now, I will fill you in on the Derby festivities!…

Apparently, this was only the 2nd annual Kentucky Derby Party held at the beautiful Harbor View Hotel where we were staying.  Since we bought our tickets in advance, we had some time to plan our outfits and hats.

Pre-party festivities…

Earlier in the day, we stumbled upon a new liquor store, Rosewater Wine and Spirits in Edgartown.  Since they were offering a Julep tasting, we had to give them a try…

Although, none of us are huge bourbon fans, the tasting was fun and the store owners were just darling!  Also, they had two sweet black labs in the store so my dog loving friend and I were all over them.

Kentucky Derby Party…

Anyway, the party at the hotel began at 5:00 and took place at the Lighthouse Grill…

Of course I was having too much fun to take a lot of pictures of the restaurant that evening. but I did take this photo the next day to show the bar area.  Such a pretty room!

Appetizers were set up all over the room while servers offered cute Derby inspired sandwiches and other treats.

The Harborview did a beautiful job decorating the room with colorful rose themed tables and other festive Derby decor.

As you can see, I opted for wine over a mint julep.  Don’t worry, there were plenty of juleps going around!

During the event, we had the chance to bet on some horses by donating to the Vineyard Montessori School fundraiser.  Each $10 donation allowed us to choose a square.

And my friend came in second, winning some wine and this pretty recycled sails bag from Sea Bags!  Just the day before, we were admiring the bags in their new Oak Bluffs store!

Here we are enjoying the party.  I know I don’t normally post many people-photos on my blog but I don’t think my friends will mind.  (At least I hope not…)

I happened to text this photo to my husband and this is the response I received back from him…

Since some of you have commented how you like his sense of humor, I thought you might enjoy that!  True, I did look like I was wearing the table cloth – kind of.  What can I say…I love navy and white!

Please note that this post contains affiliate links which means I will receive a small commission if you make a purchase after clicking on my links.

Yes, I had to put that disclaimer in there because I would love to share my outfit details with you!  I am wearing my new favorite dress with Jack Rogers gold wedge sandals.  The white hat was from Macy’s and I just threw a bow on from Michael’s.  Next year, I might go for something like this dress and I will definitely get more creative with my hat…for example…

During the evening, we had the opportunity to try on some beautiful hats displayed by the lovely ladies of Dreamboat Hats of Edgartown.  Next year, I think I’ll choose my outfit and then go to them to buy a matching hat!

Later that evening, my friend wanted us to pose for this picture with our hats (after seeing a similar photo online)…

Cute idea, but by the time we had take the photo, it was after dinner and a couple of us were already in some casual attire.  And for some reason, my friend on the right looked extra short!  I think she was leaning over laughing during the photo!

Speaking of laughing…

Before we left for our trip, I joked with my friend that I was going to combine Cinco de Mayo and the Kentucky Derby for my hat!  Don’t worry, the sombrero stayed home…

Another trip of great memories and we came home with some fun giveaways from Vineyard Vines!  And as you can see, Vineyard Selfies was also at the event with a photo booth.

And did I mention that my friend WON the prize for the best Derby ensemble?!!  She won a Vineyard Vines gift card AND a one night’s stay at the Harbor View Hotel!  Looks like we know where we are going next year!  Time to plan another Derby outfit!

Cheers!

See you next year, Harbor View!

• If you want to see more of this beautiful hotel, stop by to read my post, Favorite Hotels – The Harbor View in Martha’s Vineyard.
• Be sure to also read, Girls’ Weekend Guide to Beautiful Martha’s Vineyard to learn more about the island.

Did you watch the Kentucky Derby this year?

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