It’s 3pm in the hilltowns. Bright sunshine warms the Ashfield Lake, and the reflected light bounces up through the windows of the three-story Lakehouse, into the quiet bar and dining room.

I’ve caught the tail end of Friday lunch, and the mood at the bar is calm. A few swivel stools away, three guys sit chatting in low, relaxed voices. Two are drinking bottles of Budweiser; the third is drinking a 12-ounce pour of Ginger Libation, the hard fizzy elixir brewed by Artisan Beverage Cooperative in Greenfield.

I’m working on a buffalo chicken quesadilla, and I take a spicy, creamy bite even though the bar’s TV is playing a rather unappetizing FOX forensics drama. The quesadilla hits the spot. I grab a napkin or two, take a sip of Coca Cola, and run my hand along the old varnished wood of the long bar counter, which follows the edges of the tree trunk it was cut from.

On a recent night here, the Lakehouse was jam-packed for a David Bowie tribute concert. A visiting band that night — fronted by UMass professor Joe Pater, who performed in a white blazer and face paint as his glam stage persona Vernon Valiquette — rocked this room with some classic songs, and customers of all ages flooded the bar to request cocktails, craft beer, nachos, wings, Miller Lite, and spare quarters for the pool table.

This quirky blend of daily-grind rural life and eclectic pop-up art scene is part of what makes the Lakehouse great. It produces good food and puts on fun events. But more importantly, it brings out something special about this town and this area. The more the community puts into this place, the more it gets in return.

There are quite a few drive-ins and roadhouses in Franklin County that capture local flavor like this, but I decided to focus on three of them: the Wagon Wheel Country Drive-In, the Ashfield Lakehouse, and the Conway Inn. I embarked on a three-stop day trip — for breakfast, lunch, and dinner — to get a closer look at what makes these hilltown eateries tick. Each proved unique, but one thing they have in common: they’re all happy roadside surprises, offering worthwhile food and a pretty cool scene inside.


Let’s back up to breakfast. For that first stop, I rolled up to the Wagon Wheel, which sits along Route 2 in Gill, a 10-minute drive from the center of Greenfield and a stone’s throw from Turners Falls. Carolann Zaccara, who opened the Wagon Wheel with her husband Jon Miller almost twelve years ago, first envisioned it as an old-style drive-in like the ones she used to frequent with her parents growing up.

But the restaurant quickly morphed into what it is now: a full sit-down restaurant offering diner and comfort food as well as a few higher-end entrees and specials, which might range from seared tuna one night to pho, curry, or Chinese food the next. Visitors can settle into the cushioned booths in the homey dining area knowing know that Zaccara, who comes from a restaurant family — her siblings Maggie and Jim Zaccara own the restaurant Hope & Olive in Greenfield — can cook creatively and still hit all the good, reliable notes.

The busiest season here is summer, when the Wagon Wheel serves burgers, hot dogs, salads, and ice cream to locals and Route 2 road-trippers all day long. But even in the chillier months, Zaccara’s kitchen puts out food truck favorites like fish tacos, pulled pork, and gyro and falafel.

Then, of course, there’s breakfast, which is served Fridays, Saturdays, and Sundays. I bite into a steaming breakfast burrito, stuffed with sausage and doused in salsa, and kill my late morning daydreaming in the dining area, where unhurried customers sip coffee, chew toast and forkfuls of homefries, and chat.

“The great thing about this place is we can make whatever we want,” says Zaccara, who takes a momentary break from working the line to come sit with me at my booth. “The specials change all the time. Sometimes those entrees get up to 17 or 18 dollars — like that tuna — and I think it won’t sell at all, but it sells right out.”

The reason is simple: the Wagon Wheel’s regular customers trust the kitchen. A lot of them are locals, but with Route 2 right out the front window, Zaccara sees a lot of customers headed out from Boston and Eastern Mass to the Berkshires and Vermont. “People are very loyal,” she says. “Some only come by four or five times a year, but they’ve been doing it forever. A few of them were our very first customers.”

If the weather stays warm, business will pick back up — “these are the dark days right now,” she tells me — but even during the slow season, I’m happy to see that a drive-in known for its easy-breezy hot dogs and hamburgers has a menu hearty enough to keep people warm through the winter too.


Up in Ashfield, the Lakehouse rises from a section of private beach up to a narrow paved road. In the parking lot sits a scattering of cars, trucks, and motorcycles. The restaurant serves lunch and dinner six days a week (no Tuesdays) and the occasional brunch. This is also a popular summer spot, but it stays busy in the winter with ice fishermen and snowmobilers.

“The place had long been in the back of our minds as a community space with so much cool small-town history,” says Dre Rawlings, who bought the Lakehouse with her husband Chris early last year.

The Rawlings family has lived in Ashfield since 1999, and they had been long-time customers by the time the restaurant went up for sale. But Dre wanted to add something new and special to the Lakehouse scene. That was clear to the people of Ashfield from day one of business — the July 10 opening party last summer welcomed the Providence-based What Cheer? Brigade, an 18-piece global touring brass band. The loud, groovy nighttime bash spilled out onto the beach, with hundreds in attendance. Since then, live music has become even more integral to the spirit of the Lakehouse than it was before last year.

“I went to art school,” Dre tells me, “so our bent is very much toward the arts. When booking music, we’re keeping older local bands in the loop, and also exploring some other interests. Monthly open mic poetry. Pop-up performances. And a real mix of music.”

Dre calls the purchase of the Lakehouse a “rescue,” since the place needed a few major renovations during the two months it was closed last year. “The place needed a lot of TLC. The kitchen, the floors, the structure, the appliances — that’s where you start. Then we worked on the food. We wanted to keep it accessible, but do more things simply, with good ingredients, from scratch.”

The simplified menu offers bar favorites like hot wings, mozzarella sticks, nachos, potato skins, crab cakes, and fried fish sandwiches — plus, of course, burgers. But the entrees take it up a notch. Ranging from $13 to $22, those options include spicy pasta shells (with tasso ham, andouille sausage, blackened shrimp, jalapenos, garlic, baby spinach, and saucy tomatoes), grilled ribeye steak with potato gratin, and polenta with creamy mixed mushroom ragout over garlicky greens.

When Dre isn’t booking the live shows, she’s back in the kitchen, leading the charge and turning out plates. The Lakehouse is bound to keep evolving, she says, but so far, so good.

“Bottom line: you try to preserve what a place like this is,” she says. “This is a historic building. People have memories, and we all get attached to the way things were. So, I want people to feel comfortable, and at the same time I want this place to carry some of our personality as artists … It’s cool to run a space that can provide food, drink, and a warm atmosphere, and also do pop-up arts events. That is so my thing.”


For a casual, late dinner, I decide to take Route 116 from Ashfield back toward Interstate 91 — which lands me in the tiny, quiet downtown of Conway. It’s dark when I pull up to the Conway Inn, but the lights along the old covered porch and the neon signs in the windows beckon me toward the door of the tap room.

I push open the red wooden door and step into a small bar room. Aside from three small tables covered with red-checker pizzeria tablecloth, the rest of the room is bar counter and stools. Behind the bar, innkeeper and owner Barbara Llamas strides back and forth for her dozen customers, pouring pints from three taps (Bud, Bud Light, and a rotating BBC craft ale), putting in orders for homemade pizza, and chatting about politics and local news whenever she gets a free minute.

A poster on the wall reads “We are the 99% — Standing with Occupy Wall Street,” and Llamas is wearing a Bernie Sanders T-shirt. I’ve never met Llamas before, but she welcomes me warmly and pours me a pint. She sets it down on a rubber bar runner branded with the Patriots logo, and I take a sip before putting in an order for the bacon double cheeseburger pizza — a house special pie, piled with beef and bacon. The large bearded man sitting next to me raises his eyebrows at me and nods approvingly.

I assume he’s just a customer until Llamas hands him the order and he gets up to go back into the kitchen. After a minute, I get up to explore the rest of the main floor, which consists of a few quiet event rooms — no people back here right now — with a jukebox, pinball, two pool tables, and some quiet places to sit and play with kids while waiting for dinner to be served.

On the corkboard in the downstairs hallway, I browse the business cards for local numbers to  call for carpentry, lumber, painting, and roofing work while “Hotel California” plays from the jukebox. When Llamas has a free moment, I ask her about the upstairs. Llamas has an innkeeper’s license — she lives in the building, which she bought in 1986 — but doesn’t take boarders because she has so little spare time to change beds and see to hospitality.

“I’m always working,” she says. It’s been a labor of love for thirty years, ever since she saw the property listed in a real estate book, which she was thumbing through in a restaurant one day.

“It had been closed for a couple years,” she says. “It was looking pretty rough. It had ugly asphalt siding on it, which looked pretty crappy. But I came up and looked at it, and I loved the inside. I’ve changed the floor, but not the walls. It’s such a warm atmosphere. I haven’t changed any of that.”

The customers don’t change much either, she says. In the summers she gets more tourists passing through, but “99 percent of the people who come in here, I know.” They stop in for drinks, conversation, the occasional live music night, and the pizza nights on Fridays, Saturdays, and Sundays.

It would be easy to conclude that this tiny burb hasn’t changed much, but Llamas pointed out that property values have gone up in recent years. “We’re five minutes from I-91,” she says. “People from the universities are starting to discover Conway. It’s becoming a bedroom community. We have a lot of young professionals now.”

When I finish my pizza, Llamas hands the plate to yet another bar patron I’d assumed was just a customer. Off they go, to put my leftovers in a box for me.

“Conway’s a great little town,” Llamas tells me. “It’s an interesting mix of people. I have farmers, lots of tradesmen. Also a lot of artists. And everybody knows everybody.”

At the inn, I’m impressed to find such a warm and lively scene along a silent nighttime Main Street. In Ashfield, it’s a surprise to find a lakeside roadhouse that makes room for the avant garde. In Gill, a drive-in best known for hot dogs, hamburgers, and ice cream turns out diverse and substantive dinner fare all year round. So when planning your next day of wandering through the hilltowns, remember: just pull over, walk around, and stop in. You never know what you’ll find.•

Contact Hunter Styles at