Somehow, this October, I will be visiting all three of my favorite weekend getaways within driving distance of the D.C. area. If you’re also a local or maybe just looking to visit the Mid-Atlantic or Washington, these are three spectacular spots you might consider adding to your itinerary:
St. Michael’s, Maryland.
Stay at the Inn at Perry Cabin (where part of “Wedding Crashers” was filmed!). I’ve visited this gorgeous waterfront property with both Landon and my mother on a few separate occasions and both the hotel and the amenities are lovely, with a historic Maryland feel. It’s one of those unicorn hotels that works for romantic getaways, girls’ weekends, and family trips (we have good friends who come here with their young children every Christmas, which must be magical). I love the proximity to the Chesapeake Bay coastline, which informs the interior decor (maritime vibes, but with a recently-redone/contemporary feel) and also gives you access to their fleet of vessels, including a beautiful wood paneled skipjack. (Fellow birders: not uncommon to see heron and other water birds!) I’ve had multiple fantastic spa experiences, but the real draw for me: relaxing on the premises in different postures of recline and leisure, with the Miles River in view, whether reading in the adirondacks by the water, cuddling up by the fire pit with a glass of wine, chatting in the cozy library or nautical-themed bar, or playing bocce with a spritz in hand. Hotel guests also have access to their golf course, although Landon’s not yet played there.
Perry Cabin has a fine dining restaurant at the hotel, Stars, which specializes in Chesapeake cuisine and looks out over the water, but I personally prefer the informal Purser’s Pub. The hotel will also drive you the short five minute trip into town for a meal. We’ve enjoyed delicious meals at Ava’s Pizzeria and Bistro St. Michael’s (French), and there’s an institution called the Crab Claw (open seasonally) with the classic crab picking experience right on the water. Last fall, we sailed from Annapolis to St. Michaels with friends and our respective children and had a daydream of an afternoon at the Crab Claw, the Maritime Museum, a small playground, and JoJo’s ice cream.
Highlight activity: The Maritime Museum is fantastic and definitely worth a visit, full of local lore and nautical history. Landon and I loved visiting on our own, but it’s also highly kid-friendly, with lots to climb and explore, including the historic hexagonal Hooper Strait lighthouse.
If you’re there for a few days, drive into beautiful Easton. I would love to get to know this gem of a town better in the coming years — will share favorite spots as I uncover them, or feel free to drop recs in the comments. Easton has been referred to as “the Hamptons of the D.C. area,” with good dining and very chic people and a nearly-quaint feeling to its charming downtown area.
I’d also highly recommend looking up a local nature preserve – there are several on the Eastern Shore. Landon and I have driven the kids to visit these and they are breathtaking.
Notes on length of stay and location: This is about 90m from DC. Two nights here would be ideal.
Charlottesville, Virginia.
I’m admittedly biased since I attended UVA, but I find Charlottesville among the most magical corners on earth. It always feels like Saturday morning in Charlottesville. Quiet, a little sleepy, with rolling hills and an inherently relaxed way of being — but don’t mistake the charm for simplicity. This is a sophisticated place, with great dining, rich history, an elegant hospitality scene, and a dynamic business and entrepreneurship center. I know a lot of New Yorkers and Washingtonians who have decamped to the area over the past few years, and I completely understand the appeal. The vibe in Charlottesville falls somewhere between Southern gentility and Appalachian down-to-earthness. And it is gorgeous, with historic white columned architecture and red brick pathways against undulating countryside and centuries-old trees. There is something spectacular about the light and haze in this particular part of Virginia. I could go on and on. But you’ll just have to see it for yourself!
Stay at Keswick. Beautiful setting, gorgeous appointments, gracious common areas. The pool alone is destination-worthy! Landon actually proposed to me while we were staying at Keswick (he also played a lot of golf there in college), but the property has since been entirely renovated and upgraded, and these modifications have (in my opinion) only improved its beauty and feeling of connection to the Virginia landscape. We love to eat at Marigold, a Jean-Georges restaurant with a proper sommelier right on the Keswick property. Keswick is an AMEX partner, so if you have those perks, you’ll enjoy breakfast gratis at Marigold. Ask for one of the tables on the balcony. It is magical overlooking those golden Virginia hills in the morning.
You could spend all your time at Keswick. There is a wonderful spa (absolutely GORGEOUS relaxation room — you won’t want to leave — and steam/sauna rooms as well), a stunning pool that stays open fairly late into the season, library/billiards rooms, patios with gorgeous vistas. They have a coffee boutique as well as a charming bar and casual dining area. You could hike, you could hunt, you could play golf. The staff will arrange fishing trips for you, and you can also borrow one of their fleet of cars to go into town or drive around the area. Just driving that part of Virginia feels like a daydream, with historic farms and that breathtaking topography of farmland fading into the blue ridge.
But I’d recommend: going for a hike (use AllTrails to find a trailhead close to you — there are lots in the area), visiting Crozet (charming little strip of stores, including Bluebird + Co, where I had my recent book tour stop!, the institution known as Crozet Pizza, and Mudhouse Coffee), taking a tour of Monticello (the tours are really well done there), walking around UVA Grounds (the Lawn is iconic), or stopping at one of the local vineyards. Our favorites are King Family (charming venue), Early Mountain (probably our favorite wine), Barboursville (you can stay here, too — we’ve never done this but the rooms look gorgeous). There is also a little winery tucked away in the woods called Gabriele Rausse that we frequently visit mainly because we find the setting so idyllic. Who wouldn’t love sipping on wine while nestled among trees? Absolutely charming.
There is good shopping on the Downtown Mall (start with a coffee at Lone Light — Landon will drive out of our way to grab a cup here, and he’s a true coffee snob) and a lively college bar scene on “The Corner” (right by Grounds) that can be fun if you’re with the right crowd. For breakfast: Bodo’s Bagels.
Alt accommodations: Boars Head Inn (close to Grounds but less character unless you’re in the main building), Barboursville Cottages. Have heard good things about Pippin Hill for younger visitors but never stayed/stopped by. We have friends who put us up at Farmington Country Club (has hotel rooms on the property), which we really enjoy as well.
Notes on length of stay and location: You could easily stay and be busy in Charlottesville for several nights — we’re actually planning a family reunion here in 2026 that will run at least four nights and I know we’ll be busy the entire time! About a 2h drive from DC.
Middleburg, Virginia.
Stay at The Red Fox Inn, and go all out with the four-course dinner at the tavern. We had such a fun experience in this historic restaurant, which has a cozy, wooded, lodge-like huntsman feel, and our server was delightful. The rooms are charming, too, but I think my favorite amenity is the breakfast they deliver to your room in the morning: a charming box filled with pastries and egg sandwiches alongside a carafe of coffee. I mean! You just feel cared-for. Something so gracious about waking, making absolutely no decisions or effort, and finding a warm breakfast waiting.
Red Fox Inn is right on the main strip in Middleburg, and the stores that line it are perfection. I couldn’t have done it better if I dreamt up a fantasy small town with fabulous shopping. There is a clothing boutique called Tully Rector with the absolute best, most spot-on curation of brands and styles. Think Guest in Residence cashmere bandana scarves alongside Cara Cara cocktail dresses and Mother jeans. It’s a Magpie reader dream. But there are also loads of adorable antique and home shops up and off the strip, including Middleburg Books (a jewel box of a bookstore — walk in just to take in the charming decor and you’ll leave with dozens of book recommendations) and Bedford Lee home goods for pillows, lamps, tabletop, candles, and more. Around the corner, stop by Castle Gallery, which is an art space that curates the work of early and mid-career women artists. This is a hidden gem. You can find huge canvases of inventive, eye-catching art for under $1500. If you’re looking for a big piece for your home and want to spotlight a local artist without breaking the bank, this is where you need to go.
For dining, King St. Oyster Bar is a popular spot (crowded all day long!), but Landon and I enjoyed a lovely late lunch and glass of wine at Tremolo, where we watched all the well-appointed Middleburg-ians (Middleburgers?) walk by.
This is prime horse country, so you can look into catching an equestrian event while visiting. They also frequently have parades and community events. The vendors in the area are very tight-knit. While visiting recently, I heard about a “cookie crawl” they were coordinating on an upcoming weekend, where you stop by different stores to test different cookies.
Alt accommodations: I’ve heard mixed things about Salamander Resort, which is nearby. My mother loves it and goes 1-2x a year with one of her best friends for their spa, and I’m inclined to trust her! I’ve heard its great for families, too, with lots of activities and special attention to younger guests. Finally, people love Goodstone Inn, which is a 265-acre property a bit further off the main Middleburg drag with a renowned restaurant. I’ve never been there but it’s on my radar.
Notes on length of stay and location: 45m from DC! This is a perfect one-night visit destination.
Other Getaways to Consider.
+Growing up, we frequently drove to The Homestead in Hot Springs, VA for long weekends. My parents had a time share there, so we got to know the area really well. It’s a meatier drive — around 4h — and a harder one, too (winding roads), but the property is spectacular and there is a lot to do. There is skating in the winter, an indoor pool, formal tea, hunting and fishing, a billiards room with chess, an arcade, golf, hiking, a beautiful little Church, and they have a lot of programming. I can remember doing things as diverse as having glamor portraits taken by a visiting professional photographer to taking in a magic show? A lot happening. Great to visit for a holiday. We spent many Easters here. I can’t imagine how magical it would be for Christmas with its grand foyer!
+Auberge Primland. I’ve never visited, but this is on my shortlist. I have friends who’ve had magical visits here. It’s about a 4-5h drive from DC. We keep talking about visiting here with the kids over a fall break or a winter break of some kind.
+I’ve stayed at The Pendry in Fells Point, Baltimore several times the past few years! It was originally a cargo warehouse and has been converted into a very chic harbor-front hotel with a striking indoor garden that used to feature a gigantic bronze horse sculpture by the renowned Colombian artist Fernando Botero. Apparently the hotel has recently changed ownership (it used to be partly owned by the founders of Under Armour, a Maryland-based business), and the sculpture was removed! But still I think a beautiful place for a getaway with your husband or a girls trip. It’s right across the street from a fantastic oyster bar, Thames St. Oyster House, that I’d highly recommend.
+Deep Creek Lake. A rustic spot for classic summertime lake activities and winter skiing (at Wisp). We usually visit once in the summer and once in the winter. AirBnB is the way to go! I’ve written about a few of my favorite things to do at Deep Creek in this post.
+Inn at Little Washington. Fast for 2 days and then go all out with the full dining experience here. We’ve somehow never been here, but it’s a Washingtonian institution. Great for a milestone anniversary or celebration — not for kids. Landon and I have sort of outgrown (??) our interest in the elaborate multi-course prix fixe meals, and would prefer to have a few simpler meals while traveling, but this kind of dining does have its place. I know one day we’ll make it out here!
+Philly! Somehow only been to Philadelphia proper once in my life (!?) but did visit Villanova a few times in college to stay with friends. We had two fantastic meals on our one (recent-year) visit, though: Suraya in Fish Town and Parc on Rittenhouse Square. Fabulous venues, dining experiences, food.
OK, your turn! What other destinations would you suggest within a few hours of the DC area? (Tell us where to stay and what to do in Richmond, Easton, and other spots I’ve overlooked!)
P.S. Things I love about the Mid-Atlantic and a song for Charlottesville.
Shopping Break.
+Taffeta has been trending seriously this season (ahem, Donni pant mania) — I just ordered this chestnut-colored taffeta skirt for the season! I actually think that color is perfect for pairing with gem tones like emerald, amethyst, ruby, etc! Fab!
+This vegan leather skirt is a 10/10 gem. I got it in the chocolate color (under $200!) and the fit is AMAZING. I wore it with this alpaca tee and my Cleo boots to an event at my son’s school. I got zero pictures but I LOVED this outfit.
+Celine vibes with this perfect alpaca/wool cropped jacket. I’m in love. Imagine paired with everyday jeans like this and a great pair of suede flats.
+On the festive dressing thread: this copper velvet dress has been trending among Magpies, and Tuckernuck just released their bestselling Bessette top in a tartan. I’d prioritize the white, though, and pair with a lineup of statement skirt / pants. I now understand the hype — it’s a great, slim fit in a nice stretchy poplin material. I love the stand collar.
+I’m sorry to say it but these barrel cords from Ruti just arrived and…sigh, they are perfect. No notes. This brand knows how to cut a killer silhouette — the drape! The silhouette! You look long and lean in these. They’ve been in and out of stock the past few weeks but are worth the pre-order while available. I got them in the navy (go up one size in these!). At time of writing, their 20% off promo was still live, but if not, try code JEN15.
+Quince has a look for less for them here!
+I’m currently wearing my Ruti barrel cords with this cardigan. Frame is known for its denim (I love their slim palazzos) but I have several statement knits from them that I absolutely adore! Consider this brushed cashmere jacket and this gorgeous “doll cardi” (the buttons! the collar!). And don’t get me started on these barrel leather pants…!
+Back to slim palazzos: I found a pair on sale in a great dark rinse wash here! Most sizes available. I go up one size in these / take my larger denim size.
+Niche but people absolutely LOVE this lighted mirror for applying makeup. Could be a good solution if you don’t have a great spot to apply makeup — a makeshift area at your desk will be perfect with this. Was thinking it would be an incredible gift for a college student. You almost never have a spacious, well-lit place to get ready! Ideal for a dorm!
+Swoon – this leopard calf-hair belt.
+How CHIC are these knit Jenni Kayne pants?
+Over at Marea, my beloved sherpa hooded jacket is available for pre-order again, and they restocked their perfect bandana wrap cardigan. Try code MAREA10.
+This herringbone skirt!!! The toggles! Under $150 and screaming to be worn this fall. Dark academia vibes. Pair with a slim-fit turtleneck and loafers OR a slouchy knit and tall boots.
+On the festive statement pant front: HHH just released a beautiful fringed pair (party pants if I’ve ever seen some — imagine paired with this pink opera coat and a velvet heel OMG) and Ref added a new jacquard-trim style to their best-selling evening pants.
+Eyeing one of these bespoke button downs with my initials in the crest!
+Always keeping this under-$200 find edit up to date!
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Ah yes, the magpie-to-Wingspan-to-birder pipeline!
Thank you for all these great recs! We’ve had the Eastern Shore and Middleburg on our list for a while but we’ll add Charlottesville as well.
We also frequently go up to Baltimore (I went to boarding school in Baltimore County) and I’ve been DYING to stay at the Pendry. It’s where they filmed one of my favorite TV shows (Homicide: Life on the Street from the 90s) and the Waterfront Hotel, across the street, is owned by three characters in the show.
I’d also recommend Monkton (a similar Middleburg vibe, emphatically horsey, with great steeplechase racing throughout the year and lots to do–the NCR trail, Ladew Gardens, and great food, though it has less of a central downtown). 90 minutes from DC!