Rural Montgomery County, Maryland, is a fairly oddball choice for a trip, as people generally don't think to visit the countryside so close to the metropolis just southeast. It gets a fair amount of visitor traffic nonetheless, simply because it is so easy for residents of the close-in Montgomery County D.C. suburbs to get to. In particular, Sugarloaf Mountain is a very popular destination. But if you look a bit further and feel like wandering along quiet country roads, there are other gems to explore, be they farms where you can go picking, petting zoos, wineries, or even Maryland fried chicken.

Understand

Towns

Damascus, Poolesville, Clarksburg, and Darnestown are the main small towns in the region.

Get in

I-270 is the principal highway running through Rural Montgomery County, and I-70 runs east-west just to the north. The former is a quick way to get here from either D.C. or Frederick; the latter from Baltimore or Pennsylvania via Gettysburg.

Washington Dulles International Airport is not at all far away, although the rarely-bridged Potomac River does make it harder to get to. The fun way to get here from there would be via White's Ferry off of US-15 in Virginia by Leesburg.

Amtrak doesn't have any stops here between Rockville and Harpers Ferry, but the MARC Train Brunswick Line does have stops at 1 Boyds, 2 Barnesville, and 3 Dickerson. You will need to take a taxi, Uber, or Lyft afterwards.

See

• C&O Canal, ☏ +1 202 653-5190. This section of the 184.5-mile Chesapeake and Ohio Canal National Historical Park on its way between D.C. and Cumberland, Maryland is long and remote, with its unending bike path, beautiful river views, and isolated campgrounds awaiting. 
• 1 McKee-Beshers Wildlife Management Area (on River Rd, 2.5 miles west of Seneca Rd/MD 112, then turn left on Hunting Quarter Rd), ☏ +1 410-356-9272. While its principal purpose is as a stocked hunting range, McKee-Beshers WMA is best known for its magnificent fields of sunflowers, in bloom towards the end of July. The sunflowers were planted not for public enjoyment—they are there to attract doves for the hunt! But there are miles of trails through the fields and forest, which do connect with the C&O Canal towpath, and the WMA is quite popular with photographers. Be sure to bring heavy duty insect repellent, long pants, and good boots, as the terrain is pretty marshy. It's a good idea to give them a call to see what the hunting situation is like—it's less pleasant to walk around the fields if hunters are out in force.  
• 2 Poplar Spring Animal Sanctuary, 15200 Mt Nebo Ave, Poolesville, ☏ +1 301-428-8128. Events are somewhat monthly (check the online calendar), and feature everything from the obvious hanging out with "farm" animals to live bands and vegan potlucks. 
• 3 Sugarloaf Mountain, 7901 Comus Dr, Dickerson, ☏ +1 301 869-7846. Perhaps Maryland's best-known and most prominent monadnock, it's full of hiking trails and beautiful views over the Piedmont Plateau and towards the Appalachian Mountains. It's quite popular during the busy summer months, as it's less than an hour's drive from Washington, D.C. While a National Natural Landmark, it is a rare example of a privately owned (nonprofit) park open and intended for broad public use. Beautiful day trip. Parking is limited.  

Do

Pumpkin picking pre-Halloween

• 1 Homestead Farm, 15604 Sugarland Rd, Poolesville, ☏ +1 301-977-3761. A fun getaway for picking fruit, pumpkins, Christmas trees (or they also have a shop out front if you just want to stop by and get some great fresh produce and other farm goods). Especially if you are with kids, be sure to look for the farm animal petting zoo! 

Buy

• 1 Clarksburg Premium Outlets, 22705 Clarksburg Rd, Clarksburg (I-270 exit 18, then S on Rt 121 towards Boyds and turn left), ☏ +1 240-702-1200. M-Sa 10AM-9PM, Su 10AM-7PM. A two-level outlet store with about 90 stores, opened in 2016. Designer and name brands, food court. (updated Nov 2016)

Eat

• 1 Comus Inn at Sugarloaf Mountain, 23900 Old Hundred Rd, Dickerson, ☏ +1 301-349-5100. Lunch: F Sa 11AM-3PM; dinner: W Th Su 5-8PM, F Sa 5-9PM; brunch: Su 11AM-3PM. A beautiful, classic American, upscale dining option, with views right out the window of Sugarloaf Mountain. $35-60. 
• 2 House of Poolesville, 19611 Fisher Ave, Poolesville, ☏ +1 301-349-2935. Pan-Asian cuisine in a Victorian mansion, with frequent live bands and full bar. 

Mooin' to his own beat at Poplar Springs

• 3 Jimmie Cone, 26420 Ridge Rd, Damascus, ☏ +1 301-253-2003. April–October. 50-year-old small town soft serve ice cream joint. Cash only. Outdoor seating only. 
• 4 Red Rooster, 10005 Damascus Blvd, Damascus, ☏ +1 301-253-4081. M-Sa 5AM-9PM, Su 8AM-7PM. A hole-in-the-wall dive with what is universally acclaimed (among anyone from the area, at least) as the best fried chicken you'll ever eat. Stop by and confirm for yourself. For a treat, ask for a cherry coke—they add their own cherry syrup to regular coke, and it's twice as delicious as anything you'd get out of a can. 
• 5 Sunshine General Store, 22300 Georgia Ave, Brookeville, ☏ +1 301-774-7428. M-F 4:30AM-5PM, Sa 5AM-5PM, Su 6AM-3:30PM. This is basically a shack out in the country with incredible handmade burgers, as well as the best diner-style breakfast for miles. It's worth a stop. $3-12. 
• 6 Tom & Ray's Restaurant, 9876 Main St, Damascus, ☏ +1 301-253-3331. M-Sa 6AM-7:45PM, Su 8AM-2PM. A classic and ancient American greasy spoon in the center of Damascus. Regional plates like soft-shell crab sandwiches (in season), fried chicken, and scrapple are always good bets. Huge portions! 

Drink

• 1 Rocklands Farm Winery, 14531 Montevideo Rd, Poolesville, ☏ +1 301-825-8075. W Th 1-7PM, F 1-9PM, Sa noon-8PM, Su noon-6PM, closed M Tu. Local winery with tastings, tours, and food. (updated Apr 2023)
• 2 Sugarloaf Mountain Winery, 18125 Comus Rd, Dickerson, ☏ +1 301-605-0130. Daily noon-6PM. This is one of Maryland's most well-regarded wineries, and is easily coupled with a trip to the mountain, which in turn provides lovely views from the winery. The Comus is a favorite. Dog-friendly. 
• 3 Two Chimneys Ciderworks, 7115 Damascus Rd, Gaithersburg, ☏ +1 240-745-5390. Th 4-8PM, F 3-9PM, Sa 11AM-9PM, Su 11AM-6PM, closed M-W. Cidery built around historic chimneys. Also has gluten-free beer. Dog-friendly outside. (updated Apr 2023)

Sleep

Sunflowers at McKee-Beshers Wildlife Management Area

Surprisingly enough, there is not one place in this fair part of the county to lay one's head. You'll have to backtrack to Germantown or onwards to Frederick.

Connect

There are two public libraries out in these parts, with public WiFi and terminal use.

• 1 Damascus Library, 9701 Main St, Damascus, ☏ +1 240-773-9444. M W 1-8PM, Tu Th-Sa 10AM-6PM. 
• 2 Poolesville Library, 19633 Fisher Ave, Poolesville, ☏ +1 240-773-9550. M-W 1-8PM, Th-Sa 10AM-5PM. 

Go next

• White's Ferry across the Potomac towards Leesburg, VA was a fun outing until the ferry stopped running. If you are in the mood, Leesburg has great shopping at the Leesburg Corner Outlets.
• Historic, beautiful Harpers Ferry in West Virginia is a relatively easy drive through western Frederick County.
• Decided the country isn't for you? No worries, you hardly left the city, and it takes no time to get back to the built up Montgomery County suburbs, or for that matter D.C. via I-270 or even Baltimore via I-70. If you want somewhere in between, the small, laid back city of Frederick is close by and a nice place for a dinner or some antiques shopping.
• Past Frederick, and generally no more than an hour's drive from Rural Montgomery County is Antietam National Battlefield—a must for Civil War buffs (or really anyone with a passing interest in American History).

Routes through Rural Montgomery County

Martinsburg ← Brunswick ←	NW  SE	→ Germantown → Washington, D.C.
END ← Frederick ←	N  S	→ Merges into Brunswick Line