Stockbridge, Massachusetts, has much to offer outdoor enthusiasts and those looking for a quiet getaway.

Martha is stylish in her aqua clip-on cycling shoes that match her aqua “gravel grinder” bicycle, helmet and bicycling jersey, while I wear a T-shirt, 10-year-old sneakers, a florescent vest and a bright red helmet with attached light. We are in Stockbridge, Massachusetts, for a long weekend of reconnection and bicycling on the roads, paths and dirt lanes in the Berkshires, and Martha has plans for a full day of steep-rated climbs and awe-inspiring descents.

“There’s an outdoor pool under the oak trees, and I have some good wine,” I remind her as we take off from the Red Lion Inn, which is smack dab in the center of a town full of museums, art studios, botanical walks, and of course, near Tanglewood.

“The first hill is coming up,” she says.

We head out of town and pass Main Street mansions and eventually glide along the Housatonic River. I get mesmerized by shadowed pines, large sunning rocks, and babbling brooks and I almost forget to follow Martha.

“Gear down,” she says, as we drop off onto a dirt road aptly called Pixley Hill, which takes us directly up a rutted ledge and to a vista of mountains, meadows filled with cows, and red barns. It is a breathtaking view, but it is also a chance to catch my breath and drink some water.

We continue through the quaint villages of Alford and North Egremont and veer close to Prospect Lake, where a lone kayaker drifts along the shores. Following the Green River, we pass Barrett Woods hiking trails, and Bard College at Simon’s Rock and stop for a view of gardens and “pebble house.”

“You ready for lunch?” Martha asks, but she already knows my answer.

We cruise down a long hill into Great Barrington. Wanting to eat outside but hoping for shade and quiet, we find a makeshift garden plaza created in a parking lot which is surrounded by a plethora of bistros, cafes, and coffee shops offering pick-up service. Although I could be tempted to order a frozen Margarita, I opt for iced tea and a tall glass of water, because I know Martha has more in store for me after lunch. We order bean burritos from Fiesta Bar and Grill and eat piles of free chips and salsa.

After lunch, we adjust a “strava” app suggestion of Highway 41 and re-route ourselves to find obscure lanes with charming names like Lake Mansfield, Castle Hill, and Long Pond Road. Most turn to dirt, but the rewards are empty roads, filled with views of arboretums, fern forests, ponds, and streams. Gaggles of geese and rafters of turkey parade around us and scatter when we pass. When the skies darken in the afternoon, we are close enough to Stockbridge that we feel like adventurers zipping back to our Glen Maple cottage, just as lightning flashes.

After the storm, we finally enjoy the pool and drink wine under the oaks, and at seven, we stroll over to the outdoor courtyard filled with flower and fern.

The tables are covered with red umbrellas, and chairs lean backward for comfort. A clapboard bar is lit up in strung white lights, adding to a festive al fresco bar experience. Martha chooses a Caesar salad, while I start with watermelon and arugula dressed with pink peppercorns and a house-made vinaigrette. Candles are lit, and there are sounds of crickets coming off the meadows nearby. I pick lemon-encrusted cod with summer ratatouille and Martha goes for Bucatini alla Norma with fresh eggplant and a pomodoro basil pesto sauce. For dessert, we choose refreshing raspberry sorbets.

The next morning, after a pick-up breakfast of egg sandwiches and tall coffees, we head out again. This time, we focus on riding the backroads of Tanglewood and Lenox. We find a picturesque route along Prospect Hill. We pass Naumkeag, a 19th century “country house” with its landscaped grounds and beautiful gardens and continue onto the ridge overlooking state forests and mountain vistas. We zip over to Stockbridge Bowl, a beautiful lakeside full of sailboats catching breezes from Lenox Hills and continue toward the gravel paths of Tanglewood. No crowds, no cars and no music festivals means perfect vacancy for bicyclists. We careen past Barn Road, which leads to BSO Beach and continue through Gould Meadows and soon we are in downtown Lenox. Stately mansions, quaint bistros and a perfect place for a picnic in Lilac Park. It’s an oasis of calm – especially with artisanal coffee and blueberry scones.

“Let’s check out West Mountain Road,” Martha suggests.

And off we go again.

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Red Lion Inn. www.redlioninn.com. 30 Main Street, Stockbridge, MA. 413-298-5545. Get 30% off rates until 9/25/20; stay two or more nights and get a $100 dining credit/per room. Heated pool, year-round.

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