Decor - Travel - Lifestyle

May 11, 2017

My New Favorite Place to Watch the Kentucky Derby

In the past, we have attended Derby parties in the neighborhood or watched the race from local restaurants...but 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.  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

This girl's getaway was spent on 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.  We bought our tickets in advance so we had some time to plan our outfits and hats.

Earlier in the day, we stumbled upon a new liquor store, Rosewater Wine and Spirits in Edgartown.  They were offering a Julep tasting, so needless to say, we had to give them a try...
Mint Julep Tasting
None of us are huge bourbon fans but the tasting was fun and the store owners were just darling!  They also had two sweet black labs in the store so my dog loving friend and I were all over them.

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

I was having too much fun to take a lot of pictures of the restaurant, but I took this photo the next day to show the bar area.  Such a pretty room!

Lighthouse Grill Bar
They had a buffet of appetizers set up along with servers offering cute Derby inspired sandwiches and other treats.

Kentucky Derby Banner
The room was filled with colorful rose themed tables and other Derby decorations.

Derby Party
As you can see, I opted for wine over a mint julep but there were plenty of them going around!

Derby Party Decor

Kentucky Derby Stats
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 and won some wine and this pretty bag from Sea Bags!  These bags are made from recycled sails and ironically, we were admiring them in their Oak Bluffs store just the day before!

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

I know some of you have commented how you like his sense of humor so 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

We had the opportunity to try on some beautiful hats displayed by the lovely ladies of Dreamboat Hats of Edgartown.  I think next year I will choose my outfit and then go to them to buy a matching hat!

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
We made some great memories and 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!  It had to be fate because one of our dear friends who was supposed to join us came down with pneumonia and couldn't make it.  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!

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 stop by my post, 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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  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 in
    your 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. #Sharefest

    Amanda @ Cupcake N Dreams

  8. Looks like a blast! Girls trips are so much fun! Happy Mother's Day!! xoxo

  9. 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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