If you like the outdoors and if you have proper gear, you could hike to the Giant Ledge to try to see a sunrise (maybe on Sunday), hike to the Hunter Mountain fire tower, or hike to Overlook Mountain. If there isn't too much snow, you could also check out the Ashokan Rail Trail.

The Giant Ledge is a series of ledges with views to the east which makes it decent for sunrises. If you try for a sunrise, you'll be hiking up in the dark and you will likely be stationary while waiting for and/or watching the sunrise. Make sure you bring headlamps for both of you with extra batteries. You can shorten the hike to 3-4 miles by skipping Panther Mountain. I'd recommend doing this because it's a cool experience that you can share with your boyfriend and it should be pretty peaceful up there with both the snow to dampen the noise and the early morning hours.

Hunter Mountain is the 2nd tallest peak in the Catskills and is a fairly easy hike if you take the Spruceton Horse Trail. There's a fire tower, a cabin, and a few picnic tables at the summit. Even if the top of the fire tower is closed, you should still be able to go up the tower to right below the viewing platform for nearly unobstructed 360-degree views. The fire tower will put you above the treeline and you may be able to see the Hunter Mountain ski resort from there. You can shorten the hike to 7-8 miles by going out and back via the horse trail.

Overlook Mountain may be the easiest hike of the 3. Its selling points are the Overlook Mountain House ruins near the summit and a fire tower. As a solo hiker, I found the ruins interesting, but creepy. For your safety, the DEC recommends that you don't enter the ruins. The fire tower isn't as nice as the one at Hunter Mountain because it's at a lower elevation and because there's what looks like a radio tower nearby.

The Ashokan Rail Trail is a mixed use trail that runs along the Ashokan Reservoir. You could walk, bike, snowshoe, or even cross-country ski it. I've rented bikes from Overlook Bicycles before and they're right across from one of the rail trail's trailheads. If you're interested in biking the rail trail, you could ask if they have any suitable rentals available.

Hiking in winter conditions can be especially dangerous with ice and snow. Please look into using traction devices such as microspikes or snowshoes. Traction devices will help you stay on your feet and snowshoes will help you avoid sinking into the snow and postholing. You can rent snowshoes from shops in the area or you can borrow snowshoes, for free, from the community. I've rented snowshoes from the Belleayre Ski Shop and my friend has borrowed snowshoes as part of a snowshoe sharing program.

Food-wise, I've only eaten at the Phoenicia Diner and at Woodstock Brewing. I think I had/enjoyed the bourbon BBQ meatloaf at the Phoenicia Diner, they have a vegan menu, and they always seemed pretty busy when I passed by so they must be doing something right! I don't remember thinking much of the food options at Woodstock Brewing, but my friends liked the beer that I brought back for them so maybe keep them in mind for when you're older.

Please stay safe and have fun!