LGBT Senior’s On the Map: An Ultimate Road Trip – Winchester, Roanoke, and Savannah (Part I)

By Mark McNease
The backstory on this is a little long, so I’ll just say the genesis of the trip was to meet up with two other couples in Savannah, John and Robert, and Jean and Cindy. I don’t like flying unless I have to, and doing it for a three-night stay wasn’t appealing. I suggested instead that Frank and I drive and turn it into a long road trip. Our travel companion Michael, who often goes on cruises with us, joined the fun, so last Saturday we packed up the car and headed off for an eight-nighter that included a stop in Winchester, VA, to have lunch with Michael’s cousins and his wife, then Roanoke, Savannah, Wilmington, Baltimore, and finally home. This part I: Winchester for lunch, then on to Roanoke and Savannah.
Lunch in Winchester
This looked like a really cool town and I wish we’d have more time to spend there. A fair was going on, and the central walkway was filled with vendors. I saw a tarot card reader I would have loved to get a peek at my future from, but we had to eat and get back on the road. It was a quickie, but worth it.

Water Street Kitchen sits right in the heart of historic Old Town Winchester, Virginia, where Chef Dan Kalber turns classic Americana into something worth going out of your way for. Drawing on locally sourced ingredients to ground the menu in the region rather than the generic. The setting is informal and relaxed, with a large menu at reasonable prices and generous portions, and a vintage interior and patio that make it equally good for a leisurely lunch or a full dinner.
Then it was on to Roanoke
One of the reasons I was happy to have Michael along, apart from us being somewhat of a travel trio, was the added presence for what would amount to about 40 hours taking turns behind the wheel, not including multiple bathroom, gas, and leg-stretch stops along the way. As exciting as the prospect of the trip was, the driving itself was just as daunting. Having a third person also meant Frank would have someone to distract him from my driving, which he often expresses his opinions about.
That said, there’s a particular kind of freedom that a road trip delivers. Not the compressed efficiency of an airport, not the fixed schedule of a tour. Just you and any travel companions, multiple tanks of gas, and a slice of three of the American landscape unrolling ahead of you at whatever pace you choose to set. This particular route — our home in New Jersey to Winchester, then to Roanoke, and on down to Savannah (Part I). Then it was back up through Wilmington, and finally into Baltimore to spend a night and visit friends before heading back home to our cats and obligations.
Roanoke, Virginia: The Blue Ridge Starting Line
Roanoke is the kind of city that surprises people. Tucked into a valley in the Virginia Blue Ridge, it carries the bones of its railroad and industrial past while doing something genuinely interesting with them. The old market district has real life in it — independent shops, good food, the kind of streets worth walking slowly.
The star of the skyline, literally, is the Roanoke Star — a giant illuminated structure up on Mill Mountain that overlooks the whole valley. Go up in the evening and watch the city lights come on below you. It’s a better view than Roanoke usually gets credit for, and it costs nothing.
The surrounding landscape is the other reason to linger before heading south. The Blue Ridge Parkway runs nearby, and even a short stretch of it — windows down, speed reduced, the mountains doing what mountains do — is worth factoring into your morning before you point the car toward Georgia.
The Drive South to Savannah
Leave Roanoke heading south and you’re in for one of the more scenic highway stretches on the East Coast. I-81 through the Shenandoah Valley eventually gives way to I-77 as you cross into North Carolina, and the landscape shifts gradually from mountain ridges to piedmont to the long flat approach of the deeper South.
This is a good day to drive unhurriedly. Stop when something catches your eye. The roadside in this part of the country still has character — small towns that haven’t been entirely smoothed over by chains and franchises, county seats with courthouses that mean something, diners that have been diners since before the interstate.
The Carolinas are not just scenery to pass through. They’re the tonal shift that tells your nervous system you’re heading somewhere genuinely different.
Savannah, Georgia: The City That Takes Its Time
Savannah does not rush. This is its defining characteristic and its greatest gift to the visitor. The city’s famous grid of squares — twenty-two of them, oak-canopied and moss-draped and arranged with an almost absurd elegance — is not just decorative. It’s structural. It slows everything down. You walk differently in Savannah. You sit differently. You notice things.
The historic district is one of the largest in the country, and it wears its age gracefully rather than preciously. These are lived-in streets. People actually occupy the rowhouses and townhomes along the cobblestones. There’s a working city underneath the gorgeous surface, which is what keeps it from feeling like a museum.
The waterfront along River Street is the obvious draw, and rightly so — the old cotton warehouses converted to shops and restaurants along the bluff have a particular atmosphere, especially in the early evening when the river goes gold. But the squares are where you should spend most of your time. Sit in one. Watch the light come through the Spanish moss. Let the afternoon go by.
Plan to stay at least two nights. One is not enough.
Up next: Part II: Wilmington, Baltimore, and home







