Today’s post is all about Nantucket’s STROLL!
Now, don’t forget, if you missed SATURDAY’S POST, I included photos on that one you will not see on this post along with a little itinerary of what I did when I was alone on the island Wednesday night and Thursday. So, if you’re interested in details like that, make sure you READ THAT POST too 🙂 .
Alrighty, back to our weekend.
On Thursday morning before my family arrived, I ran some errands including…
…a trip to Bartlett’s Farm for holiday provisions 🙂 .
I drove into town around 3:00 that afternoon to walk around a bit before their 4:30 ferry came in…
The island was decked in holiday magic!
Do you see the wreath on the Brant Point lighthouse? It welcomes all that come in on the ferry.
It was the most peaceful and beautiful late afternoon on the island.
This is what the marina looks like in July…
…and here is what it looks like in December…
…oh so quiet.
I was so excited to see the ferry pull in…
…my peeps were all on it!!
We went back to the house, I made a charcuterie board, and we settled in a for a bit of holiday merry before getting ready for dinner that night.
Do you know what I loved the most? The minute we pulled in, the two littles were off finding their friends. They have two friends who are year around residents and then many other friends who are seasonal like us. They could not wait to run off and say hi to them. For the rest of the weekend, any chance they got, they were with their friends which made me SO HAPPY about our little community.
I try to wear what I only keep on the island, but for Stroll, I did bring a few sparkly things to go with what I had in my closet including…
…this super cute SEQUIN FRINGE CAMI that paired perfectly with my FAVORITE BLACK JEANS 😉 .
So fun and festive and ON SALE right now! I love how the straps are adjustable. I bought it in xs.
All ready for dinner! On Thursday night, we visited The Sea Grille and had the most delicious meal…per usual 😉 .
The next morning, Andrew, Smith and I worked out, and then Andrew made breakfast for everyone (scrambled eggs, bacon, cinnamon rolls) except for…
…my boy and me 🙂 .
The two of us went into town to sit on one of our benches and eat our very favorite breakfast together from The Hub. Spoiler alert: Mom of teen boy here would have made the entire trip over just for this one hour on the bench with my kiddo.
Around 10:30, we all decided to…
…head into town as the hustle and bustle of the weekend was beginning!
Just SO FESTIVE, right?! You guys, I wore THESE BOOTS on all four flights and all four days I was there because they’re so warm and comfy. Right now, they’re on sale discounted by more than $130 (to make them under $100!). They come in several other colors too.
We stopped for lunch a bit later after walking, shopping and looking at The Brotherhood of Thieves. Of course, Mades pulled out her fun bag which included…
…Bananagrams! Madeley James Shull is always prepared. Always.
Brotherhood is at its coziest when it’s cold outside.
After lunch…
…we continued around town…
The magic of Nantucket on Stroll weekend 🙂 .
Nantucket in June…
…and Nantucket in December 🙂 .
We headed from town to Cisco for snacks and live music at…
…The Cisco Brewery. We always, always, always love a trip to the brewery, but nothing beats a trip out there like on Stroll weekend.
It was PACKED and oh so festive and fun!
We returned home from the brewery and got ready for more festive fun back in town…
…you guys, I LOVE MY SEQUIN BOMBER JACKET! The color, the fit, the comfy-ness of it…I love it! It comes in so many different sizing options too. I bought it in “standard, xs”.
I wore THE SAME EARRINGS every night too.
We headed into town and went first to…
…the Old South Wharf because it was MAGICAL!
We ran into so many people we know here which made this stop extra fun too!
Look how fun Slip 14 was this weekend?!
We wrapped up our night with dinner at The Lobster Trap…and I guess no matter how old they get, Smith will always give her a ride 🙂 .
So the next day was officially THE 49TH ANNUAL STROLL!
What is Stroll?
It is the first weekend in December when the island “opens back up” for just a few days so that the community can come and purchase goods for the holiday season ON ISLAND as opposed to off island. Over the last 49 years, it has clearly turned in to one EPIC weekend for the island. Not only do many of the shops and restaurants open back up for the weekend (as most close mid-October and don’t reopen until almost June), but there are many fairs and craft markets where locals can sell their items to both residents and tourists alike to generate more income for the island during the off season.
We were READY to Stroll on Saturday!
We left our house at 10:00 AM ready for a full and fun day!
Walking from our house to town with my peeps in their festive gear!
Look at the real fruit in the window boxes. New England, you are beautiful in December.
I told the big kids that this was going to be our new Christmas card, but that I would photoshop them in 😉 .
These two had no problem finding the festive fun!
We visited several of the markets that were set up just for this day including this one here in the Shop and Stop parking lot.
Chicken fingers and fries before lunch? Why not?!
Agh! I love them so much!!!
Trees lined Main Street (which was blocked off from traffic on this day) and people were everywhere enjoying the festivities. They even had a stage and DJ at the top of Main playing holiday music too.
We took another selfie later and her face made me lol!
The Coast Guard brings Santa in on a boat, and then, he makes his way up Main Street on The Nantucket Hotel’s old firetruck!
Yes, it’s as charming as it sounds 🙂 .
After Santa, we spent the rest of the day enjoying the festivities in town. We had lunch…
…we watched the people…
…we enjoyed ourselves immensely.
Later that night, we enjoyed one last dinner to end the weekend.
MY TOP was extra extra festive 🙂 . I wore it with MY COATED JEANS.
We headed to The Breeze for their special Stroll dinner.
We could NOT LOVE THE PEOPLE MORE at The Nantucket Hotel & Resort (where The Breeze is located). It was a wonderful evening.
The next morning, we headed…
…back to the boat for a rainy ferry ride back to Hyannis and then on to home.
It was such a wonderful weekend!
Okay, there were a lot of questions in my DMs about Stroll, so please feel free to ask them in the comment section so that I can answer them for everyone to see. Here’s what I will say…clearly, I’m not an expert on this event nor the island of Nantucket, but in my opinion, if this is your first time visiting the island Stroll is NOT the time to visit for the weekend. In my opinion, if you’re coming over for your first visit, I would go in July, August or September when the island truly shines. During those three months, all of the shops and restaurants are open, the weather is nice so the ferry/planes have a better chance of getting over, the restaurants that are open have their full menus out. Stroll is magical, but it is a water downed version of the product you would get if you went in July, August or September (festive yet not the same).
That’s just my two cents on the subject should you be curious. Ask any other questions in the comment section please!
Merry Wednesday, friends!
Elspeth says
I’ve heard about the stroll for years! So glad you were able to go and experience it! Looks so fun!
http://www.elspethsdaybyday.com
Angela says
Sounds like such a festive weekend, Shay!! Can you share what you, Andrew, and Smith did for a workout? Do they have a gym on the island? Cardio and lift or running the beach? I’ll bet it was a nice change of pace whatever it was! Thanks for always sharing all of the fun photos with us!
Mix and Match Mama says
I ran on Thursday, but on Friday, we went to the gym there where we have a membership, and I lifted weights. I LOVE running on the island!! I never mind lifting, but being outside is by far my fave.
Andrea Conrad says
Smith is HUGE!!!
Mix and Match Mama says
Why must they grow?!
Megan Soong says
Hi Shay! Do you mind sharing where you purchased your cute Christmas hat that you are wearing in your Nantucket post? I’d love to get one. Thank you!
Mix and Match Mama says
It’s the Stroll hat that Cisco Brewery sells every year during this weekend 🙂 .
Erika Slaughter says
Looks like a special weekend away!
Shelley says
How is visiting the island in June? Is it too early or would most things be up and running?
Mix and Match Mama says
Now that I’ve lived there in June, I see the many pros and cons…and also why they call it June-uary. I would say by June 10th-ish everything was up and running, it’s just colder. Everyone kept saying the weather would drastically turn on July 1st and by golly, like magic, it did.
Cyndi W. says
I have noticed that you rarely make links to your shoes/boots and I don’t have the tech skills to figure out if they are on a separate LTK link? Please make links even if old or sold out. Thank you!
Mix and Match Mama says
Shoes are harder for me because I tend not to update those as often, so if they’re no longer available, I cannot link to anything. The boots though are not only available but on MAJOR SALE!!
Stephanie Thomas says
And now I must go watch A Godwink Christmas (Hallmark Nantucket happiness)! 🙂
sandi says
So very festive!
It is emjoyable to see pictures of the event that is featured in so many books about Nantucket. It brings Hilderbrand and Thayer books to life even more. I’m not even going to ask if there was a bribe involved that resulted in a picture of you and the teen boy. Treasure it momma, it’s a keeper and deserves a frame!
Mix and Match Mama says
There was no bribe…but he did approve it before I shared it 😉 . Some moments, he’s generous with the photos and some moments, he’s not quite. I take what I can get 🙂 .
Arika says
I love that your cute dad still wears his K-State coat!
Mix and Match Mama says
Always and forever, that man is extremely loyal 😉 .
Kacey says
Loving your cute little tree earrings and Mades photobomb in the photo with you and your is cracking me up!
Mix and Match Mama says
Thank you, thank you! They’re Bauble Bar! And Mades is a HAM!
Mary Jane McNeill says
Shay, that last top is STUNNING! How in the world are you wearing heels on those cobblestones?? I would pop an ankle! I would also suggest not visiting during FIGAWE weekend. Non-stop PARTY!
Mix and Match Mama says
You are too too sweet! Two of the nights, I didn’t really have to walk at all (we parked right at those restaurants), but one of the nights, I had to hold on to my hubby 🙂 .
Dana S. says
Your Mom is so smartly dressed and on point! I loved her red striped sweater and also her white boots. Is there any way to get a link to what she wore? Thank you!😊
Mix and Match Mama says
I know her sweater is from Loft! Her boots are Sorel. She’s always too too cute!
Ashley says
OMG. You’re living life in an Elin book! Merry Christmas! Thanks for sharing!
Mix and Match Mama says
It was like being inside one of her novels 😉 !
Lyndsey says
Oh my gosh… I loved reading this so much! All the festive vibes!!! So so fun. I also love Andrew’s shoes! Do you happen to have a link for those?
Mix and Match Mama says
They are Helly Hansen. He loves them!
Alyssa says
I think you need to be paid by Nantucket’s Board of Tourism for all the trips you have influenced people to take there over the years! Haha! I live in the Midwest and have visited twice in the past 3 years solely because of your blog!! Stroll looked every bit as festive as I imagined 🙂
Mix and Match Mama says
Awwww!! This makes me so happy!! Come visit McKinney too! I’m all about the quaint towns 😉 !
Shirley says
You’re missing a peep!
Mix and Match Mama says
We were! Kensington stayed in McKinney to do something she really wanted to do, so even though she was missed (and Facetimed A LOT!), she had fun, so that’s all that matters.
Mateya says
I have to know – have you seen Elin Hildebrand on the island yet?!
Mix and Match Mama says
One time! I saw her at a fundraiser last Stroll. I didn’t talk to her, but she was there too. She was beautiful and much taller than I expected (of course I’m small though, so everyone feels tall to me!).
Ashley Byars says
This looks fun! Did Kensington make the trip? She’s MIA from the pictures.
Mix and Match Mama says
I blogged about that last week, but she stayed behind in McKinney for something she wanted to do. We missed her!!
Kim Shannon says
Where did u get the girls Christmas shirts?
Mix and Match Mama says
Etsy 🙂
Leslie S says
love Nantucket but have never visited in the off season – it looks really fun!
Can you tell me where your candy cane stripe hoop earrings are from? They’re darling!
Mix and Match Mama says
Bauble Bar! Aren’t they fun?!
Emily Taylor says
Did you have to book reservations at the restaurants ahead of time for Stroll?
Mix and Match Mama says
YES!!
Shannon says
Looks like you had an amazing memorable weekend!
Kelley Bauer says
I want to go to Stroll so badly. I have been told it will be my retirement trip! Anyway, I would love to have your logistic ideas. Like how early to book a place to stay and restaurant reservations. Always love your posts!
Mix and Match Mama says
Awwww! What a special retirement trip! I would have your hotel booked by spring, your flights and ferry by the end of August and dinner reservations are the trickiest. We even had a hard time (and we feel like we book dining on Nantucket for living over here!). Not all of the restaurants are open, the ones that are don’t have their full menus out and all of them take reservations beginning at different times (30 days out, 14 days out, 7 days out and even day of). That part will be the trickiest detail.
Kay says
I just did the BEST mother-daughter (13 yo) trip to Nantucket this past Summer. We had such a great time so I especially loved seeing photos of how it all looks in winter! Also, side note, I LOVE that some of your clothing-shoe recommendations are now “New England tested!” It is so fun to read about TX, I love it. But I live outside Boston and am having the best time knowing that some of your clothing pics are suitable for our, ahem, much colder weather :(.
Glad you all had such a fun time!
Sheaffer says
That pic of Ashby and Madeley together with the Christmas light necklaces is too cute! They look so happy and festive!
Olesya Griffith says
This looks so fun! I was wondering if there’s any local church community that you’re a part of when y’all are there? Was just wondering if it’s a pretty secular community there? Since I know yall are believers.
Mix and Match Mama says
There are church communities there on the island (a pretty wide variety during the season especially). I’m not sure what we’ll do this summer, but last summer, we stayed plugged into our home church from the island.
Tina says
I wonder why, all these years, I thought Stroll was just a nighttime event. Like the streets lit up, etc. It looked adorable during the day with all the booths and things to do and see I just always thought it took place at night. Where I used to live, Nevada City (it was in a hallmark movie years ago), we had a thing called Victorian Christmas. It took place each weekend evening between Thanksgiving and Christmas. Carolers would dress in traditional victorian clothing and stroll the streets singing. There were big barrels with fires burning you could stand around and warm up and talk to friends. You could buy chestnuts that were roasted on site, the streets and storefronts were lit…it was magical. I thought stroll was like that.
Mix and Match Mama says
Yeah, no, it’s a daytime event (noon to be exact). Your comment makes me want to visit Nevada City though!!
Cindy Cottrell says
Is there a link for the boots your Mom was wearing. It’s a photo of your folks and you(large pail hanging above y’all. These boots are an ivory color with a fawn color on the back and what appears to be a soft sherpa or similar at the top of the boot and long shoestring (bootstring😉) thanks. ~ Cindy in VA hoping for ❄️
Mix and Match Mama says
They are Sorels. I know they’re not a recent purchase, but that’s the brand.
Deborah Leland says
I love your Nantucket posts. I live in RI and have never been to the Stroll. Do you have a hotel or B&B that you would recommend that is walking distance to the Ferry and town? I would love to go next year but would like to leave my car in Hyannis.
Mix and Match Mama says
Yes! The Nantucket Hotel & Resort is always my #1 suggestion!
Nicole says
Do you have a link for your North Face?! Thanks!!
Mix and Match Mama says
Not that one which is a shame because I love it. I bought it from the ski shop on our town square (Doug & Lynda’s).
Kelly held says
Love this post!! Do you have a link for your black boot heels or are they old?
Mix and Match Mama says
I’m sorry! They are not recent.
Heather says
Another question about something your mom is wearing.
Is there a source for the carmel color suede wedge boots she is wearing.
They are super cute! Would love to know who makes them.
Mix and Match Mama says
They’re Sorels, but they’re not current.