On Monday morning, I rode up to the fair grounds to retrieve my hall entries. I sneaked in the back, along Jane’s Fair Way, and as I turned down the dirt road, a posse of Cushing Amusement trucks — rides all folded up like inverted origami — paraded out of the field. I pulled over to let them pass and surprised myself with a lump in my throat.

Watching the rides arrive the week before the Fair fills me with excitement, even though I’m not a rides person. It just means the fair is coming.

Watching the breakdown and departure every year apparently affects me the same way that putting a dear friend on the ferry does. I am terribly sentimental about the fair.

Jeanna Shepard

In the 10, almost 11 years I’ve lived on the Island, the fair has come to represent many of the things I love about my new life on the Vineyard. (I still call it new after all this time, because it’s so starkly different from the stressful pace of life on the I-95 corridor.) My Vineyard life has given me a sense of community and a chance to experience farming, among other things. The fair does these things to a fare-thee-well. I see friends all over whenever I’m there, and I get to celebrate my own experience with farming — entering my vegetables and flowers in the hall exhibits — and to be proud of all the incredible things that friends do, from raising pigs and canning pickles to baking cakes and sewing quilts.

In case that all sounds too earnest for you, I’ll point out two other obvious benefits to the fair: It’s fun (of course). And you get to eat whatever you want.

I admit I’ve taken this license to eat a little too far some years, eating nearly every meal between Thursday and Sunday at the fair. That was all fine and good when I spent most of the summer working outdoors, but with a desk job now, this approach isn’t the smartest.

But this didn’t stop me from volunteering to write about fair food this year. What a clever move, I thought — until Thursday arrived and I hadn’t come up with a strategy, and suddenly the thought of multiple doses of fried, creamed, sizzled and sugared food seemed frightening.

I went for an extra-long walk after work and thought about it.

Jeanna Shepard

It occurred to me that despite the appeal of French fries, cotton candy and fried dough, the real food story at the fair is the number of freshly made, locally sourced, and even healthy options. Add to that the booths that raise funds for Island organizations, and you start to feel good about pigging out. Sort of.

I decided to warm up slowly and stick with my perennial favorites the first night. After all, Thursday is about sitting at the picnic tables, chatting with friends as they go by. I went straight for the vegetable tempura. A friend who joined me was more adventuresome, choosing goat curry with rice and peas from Deon’s. Touchdown Tempura benefits the high school football team, so that’s a good thing, and the tempura was particularly light and crisp this year. The portion seemed smaller, although maybe just because my friend ate half mine after finishing his curry (of which I got merely a bite). We ended the night with ice cream from the Island Children’s School booth — raspberry with chocolate chips for him, Moose Tracks for me — and a walk to the animal barn to see the oxen.

The next day I got serious about visiting local vendors. I started with Chrissy Kinsman at Pie Chicks. Year five at the fair, and she was definitely in the groove, upbeat about both summer business and the fair. “I love the fair. I get to see people I don’t see all summer; people slow down and stop to chat at the booth. It’s actually kind of relaxing compared to working in the kitchen!” she enthused. All relative of course, as Chrissy and her crew work full-out for the four days supplying the booth with freshly made pies (served by the slice, a la mode or not), cookie-wiches, and frozen pie on a stick.

Jeanna Shepard

I walked away munching on frozen key lime pie — and realized I couldn't do that at every stop. Yet it was impossible to leave a booth without a sample, so I found myself panicking, holding a half-eaten veggie burger, a half-eaten lobster roll, and a half-eaten ice cream sandwich that I didn’t want to waste. I headed for an IGI recycling station, thinking I could compost. But I ran into a friend working the station, and I noticed she was staring at the veggie burger. “Um, do you want the rest of this?” I asked tentatively. She did. I went on to offer the lobster roll and ice cream sandwich to another friend working a booth, who happily ate both. (Maybe sharing food is a Vineyard thing.)

All three of the edibles came from local folks. For Doug Smith, chef and owner of Lucky Hank’s, who offered cod cakes and sweet potato-black bean-quinoa burgers, the first year was a lot about figuring out what people like and how he could improve on what he offers next year.

The lobster roll, on the other hand, came from the oldest local booth at the fair — Bill Smith’s Clambake, now operated by Mac Cook. Mac insisted on making me a fresh lobster roll at the back of the tent, and I watched him gently mix the lobster meat, chopped celery and just a bit of mayo in a big stainless bowl. He held the split hot dog roll in one hand and said, “Bill taught me to mound the lobster—never to push it down into the roll and break it.” The chilled lobster meat, lightly dressed and perfectly seasoned, was spot on. Oddly, Mac also sells deep-fried Snickers and Twinkies. (Snickers outsell Twinkies.) Deep-fried candy bars popped up in Scotland at fish and chip shops in the 1990s, but now they’re everywhere. (For the record, deep-fried Snickers and I have never met.)

The ice cream sandwich, purchased from Popcycle, the brainchild of 17-year-old entrepreneur Noah Goldberg, featured creamy peppermint ice cream and dark chocolate chip cookies. This was Noah’s first year setting up a booth at the fair, but her business — delivering New York city-made frozen treats in Edgartown by bicycle — has gone so well that she expects to expand next year.

Jeanna Shepard

The closest I got to one of my favorite Fair booths — Josh and Angela Aronie’s Loco Tacos — was standing in the long line catching up with two old friends while they waited to order the spicy pulled chicken and marinated skirt steak tacos with cumin slaw and pico de gallo. The only longer line was the one for loaded cheeseburgers at the always popular West Tisbury Firefighter’s Civic Association booth, where I heard they were also making killer egg sandwiches in the morning for fair workers and early birds. Down there at the meaty end of the row, along with Barbecue Bill’s ribs, you could also get your grilled corn. Islanders Todd Debettencourt and Rob Baker have been shucking, grilling, and buttering between 3,000 and 4,000 ears of corn every year since 2011.

At the lighter end of the food court, I got a chance to try Yommi Healthy Frozen Treat’s superfood popsicles. Hanging out in a sweet baby-blue trailer with a surfboard atop it, proprietors Nicole Corbo and Adrian Johnson (who also operate Aloha Paddle) got their start at the Chilmark Flea. I chose a Mint Chocochip pop, made with coconut milk, local spinach and mint, local honey, raw cacao nibs, MV Sea Salt, cashews and peppermint oil.

I ate the whole thing. So when I crossed the aisle to talk with the Blissed Out folks, there was no way I could order the highly recommended Zoodle Pad Thai made with Morning Glory zucchini. Zoodles are long curly pieces of zucchini created by a spiralizer — a fun gadget to play with unless, like Jen Oliver, co-proprietor of Blissed Out with husband Fred Natusch, you’re making enough zoodles for an Ag Fair. “We’re crazy to do this,” she told me. “But we want to offer people a healthier alternative at the fair.”

Jeanna Shepard

By Sunday I thought I was done, but just in case, I bought a bag of locally made popcorn from Heidi Feldman at the MV Sea Salt booth. A collaboration with Kathleen Cowley’s Enchanted Chocolates, the corn is popped in coconut oil, then tossed with Vermont maple syrup and salt.

I proceeded to the Vineyard Gazette booth where I was on duty. I opened the bag of popcorn and three hours later it was nearly all gone. It was ethereal, I’m telling you, almost like it had no calories. Clearly, I was delirious at this point. Someone else will have to write next year’s fair food report, though I will be there as always with plenty of napkins, both for my hands and my eyes.