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!

Derby Outfits at the Harbor View Hotel

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…

Mint Julep Tasting

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…

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!

Lighthouse Grill Bar

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

Kentucky Derby Banner

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

Derby Party

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

Derby Party Decor

Kentucky Derby Stats

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.

Sea Bags (made from recycled sails)

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!

Derby Party Table

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…

Silly Text from my husband

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…

Kentucky Derby Hats

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)…

Kentucky Derby Hats

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…

Sombrero for Cinco de Mayo

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…

Derby party swag

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 - Kentucky Derby Party Girl's Weekend


See you next year, Harbor View!

Did you watch the Kentucky Derby this year?

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My New Favorite Place to Watch the Kentucky Derby


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  1. Oh my word, how fun is this. I love it. The outfits and the hats are amazing. you girls rock.

  2. OMG Shelley that looks like it was so much fun!! You look positively adorable inyour hats. It looks like a great hotel. I'm hoping to make it to the Vineyard soon. Have a wonderful Mother's Day.

  3. This looks like so much fun, Shelley! Love the hats and the dresses. The comment about your dress matching the tablecloth made me LOL. That is definitely something my husband or kids would point out to me. You looked fantastic!! Can't wait to hear more about this trip.

  4. shelley- how fun and funny ( about the comment from your hubby). going to the derby one day is on my bucket list. maybe I can borrow your hat. hope you have a great weekend!

  5. Shelley, I think you ladies had some fun! You look cute matching the tablecloth! Have a great weekend!

  6. Looks like a delightful visit to a little piece of Paradise! I love to take the Chappy Ferry, just for the fun of it!! And how can you not enjoy rocking in those aqua rockers? The party looks like it was lots of fun – especially with those cute hats!!

  7. How exciting to combine Martha's Vineyard & The Kentucky Derby all in one weekend 🙂 Your dress is beautiful. I think I've read about this hotel before. #SharefestAmanda @ Cupcake N Dreams

  8. This was a fun post. I'm glad you shared people photos of your friends and the great time celebrating Kentucky Derby. I love your dress.

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