Not to set off too many alarm bells here, Madeline, but you should be very suspicious of any grown man who's never gone hiking before. How much do you know about New Boyfriend? Is it possible he's one of those secret Russian spies planted in the United States? On the positive side, your efforts to bring a new recruit into the Legion of Those Who Relieve Themselves in the Woods is greatly appreciated, though.
Not that I usually give relationship advice in this column (though I'm perfectly willing to do it), I would suggest that you shouldn't throw New Boyfriend directly into the fire by taking him on a weeklong outdoorsy trip. If he decides that he doesn't want to answer the call of the wild after all, you'll be walking in the woods alone while he's riding a Greyhound back to DC. So start with some day trips or a weekend expedition first. Lucky for you, you're within 120 miles of the jewel of hiking in the East Coast, the Shenandoah National Park. Have you ever taken the classic seven-mile circuit loop to the top of 3,290-foot Old Rag Mountain inside the park? If New Boyfriend doesn't gape at the view of the stunning Blue Ridge from the exposed granite summit, there truly is something amiss with him (see Russian spy comment above)—and the rock scrambles leading to the top should be enough fun to bring out the kid (even in Cold War holdovers). The entire park is spiderwebbed with 500 miles of trails, including a 100-mile stretch of the Appalachian Trail, which basically follows the route of Skyline Drive along the ridge tops. Inside the Shendandoah's boundaries, there are four car camping campgrounds, and a ton of backcountry campsites hidden far from the crowds. If New Boyfriend wants a roof over his head for his first trip, you can also stay at one of the park's two rustic lodges off Skyland Drive.
Once the two of you have (hopefully) survived this first foray into the woods, you'll have a better idea of whether to take the next step: an extended stay. And I've got the perfect place for you (based on your requirement of access to other fun activities): the Adirondack Loj, outside of Lake Placid, New York. Open since 1890, it's run by the non-profit Adirondack Mountain Club, on the edge of a small wooded lake. The lodge (or Loj, if you prefer) can fit 40 people in its private rooms, bunk rooms, and loft, and it also maintains about 40 campsites, some with lean-tos (and four of which occupy prime lakefront real estate). The Loj is the hiking nexus for the incredible Vermont-sized Adirondack Park, which boasts 2,000 miles of trails that crisscross hundreds of jagged mountains, trout-filled streams, and crystal alpine lakes. Literally just outside of the rustic wooden building's back door are the trailheads for the aptly named High Peaks region of the Adirondacks, including the rocky summit of Mount Marcy, which rises above the treeline to 5,343 feet in elevation, making it New York's tallest mountain. The Loj is the perfect place to get a taste of the backcountry without forsaking civilization completely. And if New Boyfriend needs Wi-Fi access and Starbucks, he can get his fix in touristy (but quaint) downtown Lake Placid, host site for two Winter Olympics, and home to a world-class spa and resort (in case he needs a massage after sleeping on the ground) called the Mirror Lake Inn, and a handful of top-notch restaurants. If New Boyfriend still wants to go home, I suggest that he become New Former Boyfriend.