Here in the DMV, fall is an especially beautiful time of year to get engaged. The cooling temperatures, gorgeous foliage, and access to beautiful hikes mean that you can create a truly memorable moment without complicated, long-distance travel. If you’re considering a fall engagement this year (or simply looking for a quick escape from the city), we’ve put together two vetted itineraries that can serve as inspiration for your weekend getaway.

Of course, the very first step of planning your fall engagement will be to schedule your design appointment with us so that we can get the ball rolling on your engagement ring (do that now!) Once you have that step taken care of, plan your proposal trip. These suggestions will help you make the most of your weekend.

Where to go

Fortunately for us city folk, getting out to fresher air and tree-lined mountain ranges is quite easy from the DMV. If you haven’t explored outside the beltway, you’ll be happy to know that there are incredible bed & breakfasts, restaurants, and hikes within an easy drive. For your proposal weekend, we suggest you consider Sperryville, Virginia. Located just 1.5 hours outside of Alexandria and right next to Shenandoah National Park, this tiny hamlet offers a wide breadth of options. You can tailor the weekend’s activities to your own tastes. 

Itinerary One: For hikers who appreciate a cozy bed at the end of the day

Stay at The Hopkins Ordinary for a classic bed & breakfast experience that somehow perfectly blends a low-key, hiker-friendly vibe with an elevated aesthetic. This historic Sperryville landmark has been fully renovated. It projects a sophisticated, traditional style featuring antique furniture, modern bathrooms, and breezy rooms that are each uniquely appointed. From welcoming touches, such as freshly baked cookies at check-in, to the delicious breakfast that greets you in the morning, this lovely stay will provide the perfect base for your weekend in the country. 

Friday

• Arrive in the evening after work; enjoy a casual dinner nearby at The Black Twig (walkable from The Hopkins Ordinary).

Saturday

• Wake up and head downstairs to start your day with a homemade breakfast featuring locally sourced ingredients, juice, and coffee. Ask the owners for hike recommendations or strike out on your own. Personally, we love The Devil’s Staircase. Pop by the grocery across the street to stock up on picnic goods if you didn’t bring your own, and then spend the day exploring the trails. Maybe this is where you propose??

• After a day enjoying the natural splendor, head back to The Hopkins Ordinary around 4pm to enjoy their sweet Biergarten and seasonal, locally brewed beers (which are all spectacular). Feel free to head straight to the Biergarten after your hike – this is a casual, hiker-friendly environment where you can sit back and relax after a long excursion in the woods. Once you’re rested, return to your room to shower for dinner.

• If you were lucky enough to snag a coveted reservation at Three Blacksmiths, go forth and enjoy (but please don’t brag about it). Otherwise, we highly recommend walking across the street from The Hopkins Ordinary to RPK/Francis for creative cocktails and incredible brick-oven pizza, homemade pastas, and lovely salads. RPK is the food side, where you’ll find a casual, easy vibe, and Francis is where you’ll find chic cocktails in a cozy setting (you can order food from RPK at Francis). The menu is inventive, seasonal, and always tasty. 

Sunday

• Sleep in a bit before heading down for breakfast. Once you’re well-fed, check out of the B&B and hit the hiking trails again. You might want to consider a shorter hike today to reserve some time afterwards for the next stop.

• Check out Pen Druid, a brewery and cidery, before heading back to the city. Pen Druid brews its own selection of naturally fermented, very tasty beers that are always interesting to try. A sort-of-secret perk at Pen Druid is experiencing the daily offerings of Sumac, a separately owned wood-fired kitchen that operates there. Serving some astonishingly sophisticated dishes that are all locally sourced and sometimes wildly inspired, you’ll be blown away by the talent coming out of this modest-looking kitchen. Take in the gorgeous views at Pen Druid and hit the road when dusk sets in. 

Itinerary Two: For wine lovers who appreciate natural beauty, but prefer to stay out of the woods

Stay at Blue Rock Vineyard for a chic, elevated aesthetic that still feels a world away from the city. Blue Rock opened last year to plenty of excitement, and it hasn’t disappointed. The renovated inn features beautiful grounds including views of its vineyard and a peaceful pond. The rooms are deftly appointed with a trendy touch that feels modern without feeling overdone. 

Friday

• Arrive Friday evening and keep things easy by enjoying dinner at Blue Rock’s acclaimed restaurant. You can check in, settle into your room, change if needed, and simply walk downstairs for a beautiful evening in their stylish restaurant with vineyard views. Stay late and wander upstairs when you’re ready to turn in.

Saturday

• Wake up and enjoy breakfast in bed courtesy of Blue Rock. This is a time to take it easy, so read a book or go downstairs and enjoy a late morning sipping something lovely on the terrace. When you’re feeling up to it, hop in your car and take a quick drive over to Washington, Virginia (home of the famous Inn at Little Washington, of course). If dinner at The Inn isn’t in your cards, you can still experience the acclaimed hospitality offered by chef Patrick O’Connell by having lunch at his newly opened Patty O’s Cafe located just up the street from The Inn. Afterwards, stop by his little French-inspired bakery located behind the restaurant and pick up a few pastries for a light afternoon picnic on the grounds of The Inn. You can wander the area, take in the sweet farm animals, and explore The Inn’s amazing garden where they grow the produce they use at the restaurant. Maybe this is where you propose?!

• Once you have had your fill of Washington, drive back to Blue Rock and change for dinner. Enjoy a sunset glass of wine on the terrace, then pop over to The Blue Door, located in Flint Hill, Virginia. The Blue Door is also a splendid inn, but you’ll be there to enjoy their respected restaurant, which features a chef-driven menu that changes all the time. We recommend whatever pasta dish they are serving as we have yet to be disappointed by that experience.

Sunday

• Sleep in a bit and savor your last breakfast in bed of the trip. Then, pack up and drive to Early Mountain Vineyards to enjoy a lovely afternoon taking in its breathtaking scenery. Enjoy lunch at the vineyard and take home a few selections from this well-regarded winery. You’ll be glad for the souvenirs!