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Photo: LA Brown Photography
Fresh off the boat and feeling hungry? Just a five minute walk away, Waterside Market has all of your lunching and munching needs - even for the kiddos! Serving breakfast and lunch all day, ranging from fluffy chocolate chip pancakes to their famous CAB (chicken, avocado, bacon) sandwich as seen on Diners, Drive-Ins, and Dives! Waterside Market also offers crispy hand-cut fries that are arguably the best on the Island, and they even make their own chips! If you haven’t been, Waterside is definitely worth checking out, and they even offer online ordering here.

Explore Downtown
Vineyard Haven is perfect for families because everything is so close by to the Steamship Authority’s year-round Vineyard Haven ferry terminal. Even in the winter, many businesses on this quaint strip stay open, including those shops where you’ll find the perfect holiday gifts!
 A definite go-to for families is Rainy Day. This boutique gift shop offers Martha’s Vineyard souvenirs and apparel, a large children’s toy section, a plethora of self care products, greeting cards, and more! If you’re on the hunt for some unique gifts for the whole family, this is definitely a stop worth making.
Just across Main Street is Bibi’s Boutique, which specializes in children, toddler, and infant clothing and decor. Not only do their products make great gifts, but they also serve as great inspiration for your own home!
 For sport-minded families, Sideline is the perfect stop downtown! Owned by local football mom and sports enthusiast India Rose, Sideline offers motivational sportswear inspired by being on the sidelines at her own children’s games. Made with high quality materials, their unique collection of hoodies, tank tops, jackets, hats, and more is sure to please any sports fan in the family.
On the corner of Main Street sits Brickman’s, which is a favorite for locals with and without children. Originally established as a cobbler shop in 1913, Brickman’s now houses a vast inventory of apparel, footwear, and sportswear. The back of the store, however, is a toy store!
An all-time Island favorite for children is the Tisbury Toy Box. This Island classic has been operating for many years providing local and visiting children a fun and whimsical shopping experience. Offering popular new toys, games, and trinkets, Tisbury Toy Box is guaranteed to have something for everyone.
Photo: Nicole Friedler Photography
Looking for some thrills? If snow is falling in the winter months, you’ll often find families out at Tashmoo Overlook, just outside of downtown Vineyard Haven. What are usually rolling hills with a scenic view in the summer turn into the perfect sledding slopes after a good snowfall. Without a sled? Not to worry! Nearby Brickman’s also happens to sell sleds in the winter months.

 Martha’s Vineyard Museum
As you probably already know (or can imagine!), Martha’s Vineyard is known for its breathtaking views. The Martha’s Vineyard Museum is no exception! Overlooking the beautiful Lagoon Pond, this former Marine Hospital is now home to a stunning collection of Martha’s Vineyard history. The museum also is home to the first-order Fresnel Lens that was installed in the Gay Head Light for nearly 100 years! You can find this gem in the “Flashes of Brilliance” exhibit - and it is truly a sight to behold! Not to mention, just below this exhibit is the permanent “Hands-On History” exhibit, which is an interactive space for children to engage with the history of Martha’s Vineyard as well as the native species that live here.

Pet an Alpaca!
Ever wondered what it would be like to walk an alpaca? Look no further! Island Alpaca is open year-round, and offers interactive activities with fuzzy and gentle alpacas. You can pet, hug, and even walk these adorable fluff-balls, and it’s an exciting activity for the whole family. The gift shop is also a special place to find soft, hypo-allergenic gifts, such as sweaters, jackets, socks, stuffed animals, and more! The best part? In the off-season, admission is free!

 Dine & Play - at the same time! 
Can it get any better than large portions, good prices, and bowling? Located in Oak Bluffs, The Barn is a great dining experience for the entire family, and houses the only public bowling alley on the island. With a wide variety of pizza options, family-sized fried chicken buckets, and creative cocktails, this restaurant is a fun destination for visitors and locals alike

Traveling with family is almost always hard, especially when it comes to having privacy. Luckily, the Vineyard Square Hotel & Suites is open for the holidays, and offers unique “L-Shaped” rooms, which keep the beds from being side-by-side to ensure a bit of privacy. Even better, the hotel is offering discounted rooms now through the end of December. 
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