Packed Suitcase | Ask Chris: Looking for an Outdoorsy Anniversary Getaway
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Ask Chris: Looking for an Outdoorsy Anniversary Getaway

Ask Chris: Looking for an Outdoorsy Anniversary Getaway

As a fledging “mid-Atlantic travel expert,” I’ve been road-tripping around the region practically every weekend for the past year in an effort to find the best and most unique experiences the mid-Atlantic has to offer. As a result, I frequently receive emails from people looking for help planning specific travels of their own.

I’ve been responding to questions for a while now, but it just struck me that others might also benefit from my responses, too. Having just received a new query from a friend, it was decided. A new column has been born!

On to our first question…

Dear Chris,

My one-year wedding anniversary is coming up at the end of September, and it would be nice to surprise my wife with a trip somewhere local. We do Berkeley Springs every year, we have tried almost every restaurant in Baltimore, and we go camping often (we love nature.) Thus, I need something new to do within a couple hours of our Baltimore home.

Any suggestions for a good weekend or day trip that won’t cost a million dollars for a night’s stay? 


Great question! Late September is one of my absolute favorite times for outdoorsy travel in the mid-Atlantic. The weather couldn’t be nicer, which means that you can do everything from boating to hiking to brewery hopping without fear of being uncomfortable from weather that’s too hot or cold. However, keep in mind that it’s also a very popular time for local festivals—which is fun but means that hotels can really book up. So best to book soon if you want to spend the night!

Here are a few places to consider for your romantic outdoorsy anniversary getaway:


Shenandoah National Park has long been considered one of the region’s most popular fall hot-spots, but Luray’s just beginning to hit the radar of travel-savvy weekenders as a destination that offers much more than just their famous caverns.

Located off of Route 81 on Shenandoah’s western edge, Luray provides a charming home base with a small-town feel and easy access to the park’s numerous hikes and famously mountainous scenery. But adventurous activities can be found all around Luray, with outdoorsy options like kayaking, zip-lining, cycling and, of course, hiking. What I like about Luray is that after a full day of roughing it, you can come back for a relaxing evening stroll down Main Street before dinner in the heart of town.

If you want to stay the night, I’d suggest renting a cabin for the weekend. (Luray is part of the “cabin capital of Virginia,” after all!). Or, also consider a romantic B&B like Piney Hill Bed & Breakfast, a 2013 Trip Advisor Traveler’s Choice winner for under $175/night.


Downtown Luray (photo via


Luray Caverns (photo via

Fall in Shenandoah National Park

A view from Skyline Drive in nearby Shenandoah National Park



South of Luray lies Charlottesville, a Blue Ridge Mountain mecca for those in search of history, arts and a seriously good foodie scene. An urban retreat, Charlottesville is your gateway for exploring Monticello and get close to another one of Jefferson’s hobbies… wine! Evidently this founding father was also the founding father of wine in Virginia and today, the Charlottesville area’s home to a whopping 23 wineries and breweries.

In Charlottesville, you can walk along the historic Downtown Mall, stopping into shops and perusing restaurants along the way. I really enjoyed having a drink and light noshes at the dark and romantic downstairs bar at the C&O Restaurant, a local favorite. Also, outside of Charlottesville, Blue Mountain Brewery is my top pick for amazing craft beer and also boasts a popular brewery restaurant with lunch and dinner options like flatbread pizzas, burgers and sandwiches.

As far as where to stay, there are countless ultra-luxe B&B and countryside resorts near Charlottesville for those with big budgets. For thriftier travelers, embrace the UVA college spirit and check out the Cavalier Inn, where rooms start at under $90/ night. Or for around $180/ night on weekends, try the Inn at Sugar Hollow Farm, a romantic retreat that’s as sweet as it sounds, 30 minutes west of Charlottesville.

Charlottesville Historic Mall

Charlottesville’s Historic Mall

Blue Mountain Brewery

Blue Mountain Brewery




If you’re looking for a getaway that’s pure romance, the waterfront town of St. Michaels (dubbed the “Hamptons of the Chesapeake”) is my favorite early-fall option. There’s no summer beach traffic in September, so getting there is an easy trip across the Chesapeake Bay Bridge. And, once you’re there, you can park your car and forget about it because this historic town is completely walkable– just drive, park and you’ll be set for the weekend.

There are countless things to do in St. Michaels, but a few of my favorites include biking through town (pretty much every B&B offers free bikes for guests to borrow), eating creative pizzas and meatballs at Ava’s, getting out on the water in a historic Maryland skipjack and taking a walking tour hosted by the St. Michaels Museum to learn about the town’s history and about their most famous resident, Frederick Douglass. Definitely stop in for drinks at the Inn at Perry Cabin’s Purser’s Pub to sneak a peek at one of the mid-Atlantic’s most luxurious hotels.

Stay the night if you can in one of the countless B&B’s throughout St. Michaels. It’s probably going to be a little pricier than Luray and Charlottesville options, but for under $200/ night you can most likely find a B&B to fit your budget, like the Cherry Street Inn or Five Gables Inn.

Early morning in St. Michaels

Early morning on St. Michaels’ main street

HM Krentz- putting up the sails

On the water on the H.M. Krentz historic skipjack

Inn at Perry Cabin - exterior

A glimpse at the Inn at Perry Cabin




If you have any questions you’d like me to consider answering in a future “Ask Chris” post, please email me at chris [at] or add your question as a comment to this post.

And, as always, for constant inspiration, follow along as I #TravelLocal on Twitter and Instagram.

  • Melissa
    Posted at 15:53h, 13 September

    Great tips. Emailing this to a friend who recently moved to the mid-Atlantic.