Martha's Vineyard, Massachusetts

We were invited to stay at a friend's house in Martha's Vineyard for just a few days this summer, but it was enough of a taste to learn that we absolutely love it on the Vineyard and will be back again. With six distinct towns, the island is small enough to be completely manageable, yet large enough to keep us occupied and wanting to see more. Even though it's quite pricey to vacation on Martha's Vineyard, everyone we met was friendly and down-to-earth, and we really enjoyed the vibe there.

The most complicated thing about Martha's Vineyard is getting there. There are several ferry companies that service the island, but slots for ferries that will also carry your car book up fast. Fortunately, the friends who invited us to stay had ferried over their minivan, so we didn't have to bring a car. We had no trouble grabbing seats on a passenger-only Seastreak ferry, leaving from New Bedford, CT, and arriving in the town of Oak Bluffs on the island. You can always opt to rent a car on the island instead of bringing yours over.

Where to Stay

We stayed with our friends, who were renting a house through the Winnetu Oceanside Resort. The resort is absolutely gorgeous and immaculate, but it is also quite expensive. I suppose you get what you pay for. There are pools and tennis courts, plus a huge green space featuring classic lawn games and access to the beach. There's a shuttle into the nearby towns and the concierge service is amazing. I highly recommend staying at the Winnetu — if you can stomach the cost.

What to Do

One of the things I love about Martha's Vineyard is how bike-friendly it is. There are bike trails and bike stands everywhere, and this the preferred mode of transportation for many visitors. We rented our bikes over the phone from Martha's Vineyard Bike Rentals in Edgartown and had them delivered to our rental home (then later picked up) for an extra fee. It was a lovely service!

There are dozens of public beaches in Martha's Vineyard, and we spent a day at beautiful State Beach. Approaching the beach after parking on the side of the road, the waving beachgrass gives way to a narrow strip of sand that stretches on for two miles. Beyond that are calm, clear, shallow waters.

There's a small bridge by State beach that connects the towns of Oak Bluffs and Edgartown. It's dubbed Jaws Bridge, as the movie Jaws was filmed in Martha's Vineyard, and people can be seen jumping from the bridge's wooden railing all day long — it's sort of a Martha's Vineyard tradition. The 11 year olds in our group were able to make the jump into the salty sea, but my 9-year-old backed out at the last minute.

For a very different beach experience, we drove out to Aquinnah beach (formerly known as Gay Head beach) one evening. After parking in the lot or on the side of the road, you can walk up to an overlook to catch the sunset from a platform situated on a cliff, or hike about 10 minutes down to the beach to enjoy the sunset, with the crashing ocean as the soundtrack. We did the latter and really enjoyed the experience. From this beach, you get a prime view of Aquinnah's famously beautiful clay cliffs.

After the sun disappeared from the horizon, we doubled back and additionally walked up to the overlook to admire the views from there. There's a restaurant there called The Aquinnah Shop, which features a deck that would've been perfect for watching the sunset. Maybe next time we'll manage to get reservations!



For a completely different experience, we strolled through the charming Gingerbread House village in Oak Bluffs, where we saw hundreds of tiny Victorian cottages that are exquisitely decorated and painted. The houses resemble dollhouses and can be rented during the summer. Situated in one of the gingerbread houses is the Cottage Museum, which offers a glimpse of the interior and tells about the history of this adorably quaint section of Martha's Vineyard.

Two things we didn't get to do while we were there, but will try to get to next time, are visiting the alpaca farm Island Alpaca and riding the merry-go-round at Flying Horses Carousel.

Where to Eat

There's so much good seafood to enjoy in Martha's Vineyard. We dined al fresco at The Seafood Shanty in Edgartown one evening, where the ambience and local oysters were out of this world. Another evening we bought hot and cold lobster rolls from the no-frills fish market Edgartown Seafood and ate on the deck in our backyard.

There are many cute little ice cream shops to choose from in Martha's Vineyard, but only Ben & Bill's in Oak Bluffs serves lobster ice cream, which I admit to being too intimidated to try. (The ice cream is butter-flavored, with chunks of real lobster mixed in ... yum?) Also popular is the more traditional homemade ice cream flavors of Mad Martha's, which has three locations in Martha's Vineyard: Edgartown, Oak Bluffs, and Vineyard Haven.

In Oak Bluffs, we ate our last meal at Nancy's Restaurant (love the name) before climbing aboard our ferry to return to the real world. Famous for being one of President Obama's favorite places to eat on the Vineyard, Nancy's is a no-frills seafood place with a cute indoor area and picnic tables on the outside. My fried shrimp plate was very tasty!

What's Nearby

Just a ferry-ride away from Martha's Vineyard is Cape Cod, which we also love (and is a lot more affordable!). Here's my itinerary for that area.

You might also like:

Cape Cod with Kids: What to Do, See, and Eat

7 Kid-Friendly Factory Tours

I admit to being a sucker for factory tours. I know they're tourist traps, but there's just something about seeing the place where a familiar product gets made that really appeals to me. And the fact that most food-related factory tours involve products that my kids crave because they only get them as treats makes it easy for me to convince the whole family to come along. Here are six factory tours that we've experienced across the country.

Cape Cod Potato Chips, Hyannis, Massachusetts
This is a straight-up view of the factory, with no real bells or whistles. The cool part is that you get to see the whole operation, from the salting of the potato chips to when they get bagged by a machine, and you get a free bag of potato chips at the end. But there are no interactive elements, and the whole thing is self-guided. Still, it’s pretty neat to be able to eat fresh Cape Cod potato chips while in Cape Cod!

Ben & Jerry's Ice Cream, Waterbury, Vermont
What you get here is a half-hour guided tour, plus a scoop of ice cream at the end. Not bad for just $4 per adult (kids under 12 are free). This is a popular stop for tourists in the area, so it may get crowded during high season. A private ice cream making session can be scheduled in advance on certain days (we didn't try it).

Hershey's Chocolate, Hershey, Pennsylvania
The good news is that this tour is free and features a fun, sit-down ride that takes you through the history of Hershey's chocolate making. The bad news is that you'll need to stand on line to get on the ride, since Hershey is always overrun by tourists. Add on the "create your own chocolate bar" experience, which is pricey but well worth the money.

Turkey Hill Ice Cream, Columbia, Pennsylvania
The Turkey Hill Experience is well worth a visit if you’re in the Lancaster area. Milk a mechanical cow, drive a milk truck, taste unlimited ice cream and iced tea samples, and make your own ice cream flavor, which you then get to take home. Bring a cooler to keep your pints cold during the ride back!

Pez Candy, Orange, New York
Visit the place that dispenses Pez dispensers. Admission for adults is $5, but you get a $2 credit toward anything from the gift shop, so that seems pretty fair. Candy demos are offered on weekdays, and free samples are available all the time. Naturally, the collection of Pez memorabilia that's housed here is off the hook! Be prepared to feel nostalgic.

Jelly Belly Candy, Fairfield, California
This is a fantastic (and free!) guided factory tour, one of the better ones that we’ve been on. Of course, that just meant we ended up spending way more than we should've on candy after the tour. It shows you the whole operation floor and features cute, informative games along the way. On the way out, you get a free bag of jelly beans. And if that weren't enough, you can try unlimited flavors at the jelly bean bar.

Vermont Teddy Bear, Shelburne, Vermont
I highly recommend this tour for your kids — if you can stomach the steep price ($40+) of a Vermont Teddy Bear from the gift shop afterwards (because your kids will definitely be begging for one). A "bear ambassador" walks you around the workstations of the factory, where you'll get to see craftspeople hand-making the bears on weekdays (or their unmanned sewing machines on the weekends). The tour is hands on, with opportunities to touch the fur and stuffing, and you leave with a souvenir bear button. Adults are $4 and kids under 12 are free.

Any great factory tours that I missed? Let me know in the comments section!

You may also like: 

Lancaster with Kids: What to See, Do, and Eat

Cape Cod with Kids: What to See, Do, and Eat

Sonoma with Kids: What to See, Do, and Eat

Chatham, Massachusetts

Cape Cod's many towns each has its own distinctive personality, and we picked Chatham for its plentiful children's activities and location smack in the middle of the Cape.

What to Do

See the fishing boats come in on Chatham Pier, and them watch them unload their catch up close – the kids loved this activity so much we were on the dock for almost an hour. There are also seals swimming around the pier, and a takeout window for lunch, selling Cape Cod staples: lobster rolls, fish and chips, chowder.

Chatham's got plenty of beaches to choose from, but we loved three in particular. The expansive Chatham Lighthouse Beach isn't good for swimming, but it's the perfect place to take a stroll, as it's got the finest sand I've experienced outside of the Caribbean and a beautiful view of the namesake lighthouse towering in the background. For a relaxing afternoon at the beach, check out Harding's or Cockle Cove, both offering calm, warm, shallow waters – in other words, they're perfect for small children.

On summer Fridays at 8pm, the Chatham Town Band sets up in the gazebo at Kate Gould Park on Main Street and delivers an old-fashioned outdoor concert. Claim a spot early with your folding chairs and blankets, and come back after dinner.

And you'll have to make a stop at Chatham Candy Manor, which is always packed with people coming from all over the Cape to buy the fudge, hand-dipped chocolates and bagged gummy candies.

Where to Eat

A really neat place to grab breakfast or lunch is Hangar B Eatery, an extremely kid-friendly restaurant offering organic and local ingredients and a view that can't be beat – it's adjacent to the tiny Chatham Airport, so you can watch small planes take off and land while you wait for a table.

We also loved eating at Brax Landing in nearby Harwich Port, which features a beautiful outdoor deck overlooking Saquatucket Harbor. The food is excellent and the ambiance is just the right mix of casual and preppy.

For ice cream, head over to neighboring Yarmouth, where you'll find the super popular Cape Cod Creamery, with its wraparound porch and Adirondack chairs to lounge on, and the small but yummy Lil' Caboose, which has a wooden train set up on the premises that the kids will love.

What's Nearby

The highlight of our trip was to go on a fishing tour with Cap'n Kids Fishing Adventures in Harwich Port. The tour guarantees that your kids will catch fish during the two-hour boat ride – and they were totally right! The kids had a blast using the fishing poles, watching the lobster and crab traps getting pulled in, and scrubbing the deck.

For other New England itineraries, check out my posts for Kennebunkport, Maine, and Newport, Rhode Island.