Top 10: Martha's Vineyard Musts

Back in January, I celebrated 10 years of Pop.Bop.Shop. At that time, several readers suggested that I share Top 10 lists of my best discoveries from the past decade. I loved the idea so much, I decided to publish a new list every month in 2019. In case you missed any of the earlier round ups, you can catch up here:

This month, I'm excited to share my recommendations for a memorable trip to Martha's Vineyard. Whether you go as a day trip, for a weekend, or for the entire summer, I hope to arm you with a list that helps you make the most of your time on the island.

We're going to do this David Letterman-style, starting with #10 and working our way to #1.

10. Black Dog Tavern (Vineyard Haven)

Black Dog is one of the most iconic places on the Vineyard, and its fame has extended thanks to a line of impossible-to-resist merchandise!

The restaurant is just steps from the Vineyard Haven ferry stop, making it super easy to hop off the boat and head straight to lunch or dinner.

Black Dog Tavern

The tavern offers a great cocktail menu (I went with a Bloody Mary during my visit), and tasty food selections too.

Black Dog Tavern

We had the blackened burger and the quinoa patty, both delicious and served with mountains of steak fries.

Black Dog Tavern

The best part of the dining experience is the view. How can you beat this?

Black Dog Tavern

Of course we went into the merch shop after lunch and I walked away with a sweatshirt that has become an absolute wardrobe staple. I couldn't find my exact style online, but these two (Hadley Cowlneck and Chappy Cowlneck) and very similar.

9. Flying Horses Carousel (Oak Bluffs)

I grew up going to the Paragon Park Carousel in Hull, MA, so whenever I see one, I have to take a spin. The Flying Horses Carousel in Oak Bluffs is the oldest in the country, opening in 1876.

Flying Horses Carousel

It costs $3 dollars for a ride. While you're waiting in line, you get to observe the special feature of this particular carousel - the quest for rings. Before each ride begins, the staff fill two wooden arms with rings and as you ride around, you try to snag as many as you can. During each ride there are two brass rings hidden in the lot and if you catch one, you win a free ride.

Flying Horses Carousel

We were excited to have the experience, but for the little kids on the ride, this was a serious competition! Look how many the girl next to me was able to grab:

Flying Horses Carousel

The carousel is super close to the Oak Bluffs ferry stop, so if you arrive to that pier, this is a fun place to begin your vacation.

8. Aquinnah Lighthouse (Aquinnah)

There are many lighthouses on the island, but there is only one set above stunning, red clay cliffs, and that's in Aquinnah. Though the day we went it was a bit foggy, the natural beauty of the area was still undeniable.

Aquinnah Lighthouse

While at the lighthouse, you can enjoy a meal at Orange Peel Bakery & Cafe or Cliffhangers - both tiny and adorable spots.

Aquinnah Lighthouse

7. L’etoile (Edgartown)

There is one reason people go to L'etoile, and that's for the "Startini."

The drink is citrus vodka, cointreau, lime juice, pomegranate purée and prosecco.

The restaurant is located on the first floor of the Sydney Hotel in Edgartown and it has a wonderful front porch where you can sip your cocktail and enjoy the people watching.

If you have a late dinner reservation, beginning the evening at L'etoile for a drink is the perfect way to soak up the magic of Edgartown.

6. Quansoo Beach (Chillmark)

I was looking forward to going to the beach in Martha's Vineyard, because I've spent so much time on other New England beaches and I wanted to see how it would compare. Quansoo is one of the quietest beaches I have ever set foot on.

Quansoo Beach

We went in the late afternoon, and used the time to walk, rather than set up a compound for the full day.

Quansoo Beach

It was so peaceful. I felt like I could have stayed there forever.

5. Makonikey Beach (West Tisbury)

Now, I have to preface this by saying I had the pleasure of experiencing this view at someone's private home, so while this identical spot isn't open to the public, you can still access this beach.

During my most recent Vineyard visit, I had the honor of attending a happy hour at a friend's parents' home in West Tisbury.

West Tisbury

In addition to the wine and cheese, we also got to take in one of the most exquisite views I have ever seen in all 34 years of my life.

West Tisbury

Mother Nature also gifted us a multi-colored sunset that night too.

West Tisbury

4. Harbor View Hotel (Edgartown)

If you're at the age where you have a lot of friends getting married, chances are you have been to the Harbor View Hotel in Edgartown, or at least seen pictures of it. The front porch is lined with rocking chairs, the ideal spot to order a glass of wine and watch the sunset.

Harbor View Hotel

I took this photo from one of those rocking chairs:

Harbor View Hotel

Rather than stay at the hotel (which is quite pricey), look up the time for sunset, and plan to snag one of those rocking chairs about 30 minutes before. You won't be sorry!

3. Chesca's (Edgartown)

We had many epic meals during our Martha's Vineyard trip two summers ago, but my favorite was dinner at Chesca's.

The front porch has a row of rocking chairs (are you sensing a theme here?), the perfect place to wait for your table or enjoy a pre-dinner drink.

Chescas

We were a party of six, and every single person loved their appetizers and entrees.

Chescas Chescas

Two friends took advantage of Chesca's amazing (and if you ask me, genius) menu special called the bento box. Bento boxes are most commonly offered at Japanese restaurants and allow diners to sample many things on one tray.

At Chesca's, they've adopted this approach and you can order a soup (clam chowder or Tuscan white bean), salad, mashed potatoes, sauteed veggies and a choice of protein (salmon, shrimp or chicken). This way, if you kind of want clam chowder, but you also want a salad and maybe you're also intrigued by a piece of fish, you can have every single one of those menu items. It's brilliant.

Chescas

2. Gingerbread Houses (Oak Bluffs)

You cannot go to Martha's Vineyard without making time to wander through the Gingerbread Houses in Oak Bluffs.

Gingerbread Houses

Though it seems impossible, people actually do live in these!

Gingerbread Houses

They are too cute for words, and often have very charming details.

Gingerbread Houses

I had the best time walking alongside each one of these precious cottages. Strolling through this community is awe-inspiring for grownups and kids alike!

1. Edgartown Lighthouse (Edgartown)

Of all the places I have gone on the Vineyard, the one that took my breath away was the Edgartown Lighthouse.

From the street, you walk down a short path to the sand and poof! You're right there.

Edgartown Lighthouse

We arrived just as the sun was beginning to set. We sat right on the beach, taking in our surroundings. From that spot, you can watch the boats go back and forth to Chappaquiddick.

Edgartown Lighthouse

We learned very quickly that the lighthouse (and the beach) is a popular photo shoot spot. We saw a Vineyard Vines-clad family with a photographer, a newly engaged couple with two camera people, and a group of 10 high school girls snapping up a storm.

When in Rome, right?

Edgartown Lighthouse

There you have it! My Martha's Vineyard Musts.

Tell me, what else what you add to the list?

Comments

seoservices

Fri, 07/02/2021 - 12:04

Mohammad Taha

Fri, 07/02/2021 - 12:04

An interesting dialogue is price comment. I feel that it is best to write more on this matter, it may not be a taboo topic however usually individuals are not enough to talk on such topics. To the next. Cheers. best online casino in canada

seo services

Fri, 07/02/2021 - 12:35

Hello I am so delighted I located your blog, I really located you by mistake, while I was watching on google for something else, Anyways I am here now and could just like to say thank for a tremendous post and a all round entertaining website. Please do keep up the great work. casinospill på nett

seoservices

Sat, 07/03/2021 - 06:59

Merely a smiling visitant here to share the love (:, btw outstanding style. i99pro

seoservices

Sat, 07/03/2021 - 07:43

nice post, keep up with this interesting work. It really is good to know that this topic is being covered also on this web site so cheers for taking time to discuss this! i99pro

Mindest Mint

Sat, 07/03/2021 - 11:55

seoservices

Sun, 07/04/2021 - 07:55

Cool stuff you have got and you keep update all of us. esa letter

Mindest Mint

Sun, 07/04/2021 - 09:42

This is a truly good site post. Not too many people would actually, the way you just did. I am really impressed that there is so much information about this subject that have been uncovered and you’ve done your best, with so much class. If wanted to know more about green smoke reviews, than by all means come in and check our stuff. esa letter

Ruth Dean

Sun, 07/04/2021 - 15:33

Great Information sharing .. I am very happy to read this article .. thanks for giving us go through info.Fantastic nice. I appreciate this post. 스포츠토토

Ruth Dean

Sun, 07/04/2021 - 16:03

Hi, I find reading this article a joy. It is extremely helpful and interesting and very much looking forward to reading more of your work.. 스포츠토토

Mohammad Taha

Mon, 07/05/2021 - 09:59

I really like your writing style, great information, thankyou for posting. 안전놀이터

Mindest Mint

Tue, 07/06/2021 - 05:32

Nice to be visiting your blog once more, it has been months for me. Well this article that ive been waited for therefore long. i want this article to finish my assignment within the faculty, and it has same topic together with your article. Thanks, nice share. 토토사이트

Mindest Mint

Tue, 07/06/2021 - 11:55

i am always looking for some free stuffs over the internet. there are also some companies which gives free samples. บาคาร่าออนไลน์

seoservices

Tue, 07/06/2021 - 13:02

I can’t imagine focusing long enough to research; much less write this kind of article. You’ve outdone yourself with this material. This is great content. บาคาร่าออนไลน์

Mohammad Taha

Wed, 07/07/2021 - 11:25

Keep up the good work , I read few posts on this web site and I conceive that your blog is very interesting and has sets of fantastic information. visit this page

Mohammad Taha

Fri, 07/09/2021 - 13:03

Great post, you have pointed out some fantastic points , I likewise think this s a very wonderful website. 바카라검증

Mindest Mint

Sat, 07/10/2021 - 06:00

NIMRA SHAIKH

Sat, 07/10/2021 - 07:22

The information you have posted is very useful. The sites you have referred was good. Thanks for sharing.. 4k stogram

Ruth Dean

Sat, 07/10/2021 - 12:46

I have read your article, it is very informative and helpful for me.I admire the valuable information you offer in your articles. Thanks for posting it.. Unattended Death Cleaning Services

Mindest Mint

Sun, 07/11/2021 - 01:42

Impressive web site, Distinguished feedback that I can tackle. Im moving forward and may apply to my current job as a pet sitter, which is very enjoyable, but I need to additional expand. Regards. 메이저사이트

seoservices

Sun, 07/11/2021 - 07:24

seoservices

Sun, 07/11/2021 - 21:22

Mindest Mint

Tue, 07/13/2021 - 10:47

I am unable to read articles online very often, but I’m glad I did today. This is very well written and your points are well-expressed. Please, don’t ever stop writing. 토토커뮤니티

Mohammad Taha

Thu, 07/15/2021 - 12:07

asim seo

Fri, 07/16/2021 - 11:21

Thank you very much for keep this information. moon rocks drugs

Mindest Mint

Fri, 07/16/2021 - 13:09

Thanks for the blog loaded with so many information. Stopping by your blog helped me to get what I was looking for. 카지노사이트

Mohammad Taha

Sat, 07/17/2021 - 02:18

Good website! I truly love how it is easy on my eyes it is. I am wondering how I might be notified whenever a new post has been made. I have subscribed to your RSS which may do the trick? Have a great day! https://www.khmertimeskh.com/50824199/chen-zhi-and-prince-group-commit-3-million-to-help-cambodia-combat-rising-covid-19-caseload/

Mohammad Taha

Mon, 07/19/2021 - 02:00

I am jovial you take pride in what you write. It makes you stand way out from many other writers that can not push high-quality content like you. 먹튀검증

Mohammad Taha

Tue, 07/20/2021 - 15:15

Good artcile, but it would be better if in future you can share more about this subject. Keep posting. poker 88

seoservices

Wed, 07/21/2021 - 14:54

What is an outstanding post! “I’ll be back” (to read more of your content). Thanks for the nudge! source

Mohammad Taha

Thu, 07/22/2021 - 08:53

I am jovial you take pride in what you write. It makes you stand way out from many other writers that can not push high-quality content like you. http://www.shuttlesky.in/small-capsule-lift-home-price-india.html

seoservices

Thu, 07/22/2021 - 09:09

Pretty nice post. I just stumbled upon your weblog and wanted to say that I have really enjoyed browsing your blog posts. After all I’ll be subscribing to your feed and I hope you write again soon! shuttlesky

seoservices

Sat, 07/24/2021 - 06:03

Remarkable article, it is particularly useful! I quietly began in this, and I'm becoming more acquainted with it better! Delights, keep doing more and extra impressive! halal bakery delivery

seoservices

Sat, 07/24/2021 - 11:24

Wow, What an Outstanding post. I found this too much informatics. It is what I was seeking for. I would like to recommend you that please keep sharing such type of info.If possible, Thanks. 안전놀이터

Mohammad Taha

Sat, 07/24/2021 - 13:42

I got too much interesting stuff on your blog. I guess I am not the only one having all the enjoyment here! Keep up the good work. 토토사이트

seoservices

Mon, 07/26/2021 - 05:04

Wow, What an Outstanding post. I found this too much informatics. It is what I was seeking for. I would like to recommend you that please keep sharing such type of info.If possible, Thanks. katmovie

Mohammad Taha

Mon, 07/26/2021 - 05:11

Hi there! Nice post! Please tell us when I will see a follow up! openload

seoservices

Mon, 07/26/2021 - 07:23

seoservices

Mon, 07/26/2021 - 10:16

Someone Sometimes with visits your blog regularly and recommended it in my experience to read as well. The way of writing is excellent and also the content is top-notch. Thanks for that insight you provide the readers! worldfree4u

NIMRA SHAIKH

Mon, 07/26/2021 - 11:40

I am very happy to discover your post as it will become on top in my collection of favorite blogs to visit. BTC Canada

Mohammad Taha

Tue, 07/27/2021 - 05:40

A very excellent blog post. I am thankful for your blog post. I have found a lot of approaches after visiting your post. india matka

seoservices

Tue, 07/27/2021 - 05:41

Hi there! Nice stuff, do keep me posted when you post again something like this! matka resut

Mohammad Taha

Tue, 07/27/2021 - 09:08

Wow, What an Outstanding post. I found this too much informatics. It is what I was seeking for. I would like to recommend you that please keep sharing such type of info.If possible, Thanks. matka

seoservices

Tue, 07/27/2021 - 09:17

I am unable to read articles online very often, but I’m glad I did today. This is very well written and your points are well-expressed. Please, don’t ever stop writing. kalyan satta

asim seo

Tue, 07/27/2021 - 10:43

I haven’t any word to appreciate this post.....Really i am impressed from this post....the person who create this post it was a great human..thanks for shared this with us. Hijabi gamer

Mohammad Taha

Wed, 07/28/2021 - 04:56

nice post, keep up with this interesting work. It really is good to know that this topic is being covered also on this web site so cheers for taking time to discuss this! 스포츠중계

seoservices

Wed, 07/28/2021 - 06:05

I think this is one of the most significant information for me. And i’m glad reading your article. But should remark on some general things, The web site style is perfect, the articles is really great : D. Good job, cheers Canninghill Piers

Mohammad Taha

Wed, 07/28/2021 - 06:14

i am always looking for some free stuffs over the internet. there are also some companies which gives free samples. The Commodore Condo

Mindest Mint

Wed, 07/28/2021 - 13:15

Took me time to read all the comments, but I really enjoyed the article. It proved to be Very helpful to me and I am sure to all the commenters here! It’s always nice when you can not only be informed, but also entertained! 에볼루션카지노

Mindest Mint

Wed, 07/28/2021 - 15:09

Hi there! Nice stuff, do keep me posted when you post again something like this! bolly4u