Self Guided Walking Holidays & Cycling Holidays

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Explore Shenandoah National Park


  • Hike the highlights of Shenandoah National Park to waterfalls and rocky summits
  • Experience where southern hospitality meets mountain character in the heart of Appalachia
  • Travel back in time at Thomas Jefferson’s Monticello, a UNESCO World Heritage Site
  • Drive the famous 105-mile Skyline Drive, stopping to photograph idyllic vistas
  • Visit the sleepy hamlet of ‘Little Washington’, tucked into the foothills of the Blue Ridge Mountains

Spend a week exploring the highlights of Shenandoah National Park. Pair a drive along the meandering Skyline Drive, which contours the park’s ridgeline, with day hikes showcasing the best of the park. Follow a cascading creek, hike to a towering waterfall, and tackle a rocky summit for views in all directions.

Begin your tour with a hike back in history to Thomas Jefferson’s Monticello, on a full day in the charming city of Charlottesville. Then head into the Blue Ridge Mountains to make the iconic drive. Stop to snap a photo at one of 75 scenic lookouts, hit the trail for a hike on our favorite Shenandoah circuits, and at day’s end rest your feet at a historic park lodge.

Gain a new perspective of the mountains as you drive among the rolling farm fields and idyllic hamlets below. A two-night stay in Little Washington will provide the perfect finale for the week, including a visit to a local distillery and a corner of the world where time seems to have stopped—at least for now.

Day 1: Arrive Charlottesville

Fly into Charlottesville, Virginia and pick up your rental car for the 20-minute drive into town. Explore the culinary options tonight; for a small city, Charlottesville has impressive farm-to-table and international cuisine.

Overnight: Charlottesville

Day 2: Hike Monticello Trail & visit grounds

A short hike on the Monticello-Saunders Trail will take you through both space and time to the historic and architectural marvel, Monticello, home of the nation’s third president. Based on Italian design principles, Thomas Jefferson’s estate is now a UNESCO World Heritage Site (along with University of Virginia’s ’academical village’, another of his projects).

If you haven’t had the chance, leave time to wander Charlottesville’s downtown pedestrian mall, lined with restaurants and shops.

Hike: 4 mi +/- 300 ft

Overnight: Charlottesville

Day 3: Hike Jones Run—Doyles River Loop; Optional Hike to Stony Man

Get your first taste of Skyline Drive, the 105-mile road that winds along the crest of Shenandoah National Park. Keep an eye out for wildlife as you travel through ideal black bear habitat and white-tailed deer country.

An hour from the city, but a world away, is the Jones Run—Doyles River Loop. Walk to the music of the cascades, stop to picnic along the creek, and follow the circuit back to your car. Another hour north you’ll find your home for the next two nights at an historic summer resort from the 1920s.

Hike: 6.5 mi +1400 ft

Optional Hike (from lodge): 1.6 mi +/-350 ft

Overnight: Skyland Lodge, Shenandoah National Park

Day 4: Hike Rose River Loop; Optional Hawksbill Summit Hike

Continue touring the Park’s many cascades with the Rose River Loop, where you’ll encounter 67-foot Rose River Falls before following Hogcamp Branch back up to the ridge. Never far from a babbling brook, this hike offers tranquility and excitement in equal parts.

The Hawksbill Summit hike is short but sweet, and highly recommended, as Hawksbill is the highest point in the park. A rock platform was built here by the Civilian Conservation Corps and provides a perfect climax for the out-and-back journey.

Hike: 3.8 mi +/-870 ft

Optional Hike: 2.8 mi +/- 660 ft

Overnight: Skyland Lodge, Shenandoah National Park

Day 5: Hike Nicholson Hollow—Corbin Cabin Loop; Optional Hike Mary’s Rock

Descending via Nicholson Hollow, your loop hike for the morning offers an interesting place for a break at the Corbin Cabin, listed on the National Register of Historic Places. But don’t linger long because if you have the energy, Mary’s Rock is a worthwhile side trip on your drive this afternoon, offering views to the west and north.Cruise along the northern end of Skyline Drive before dropping down out of the mountains and into the farmland of the Virginia Piedmont (the plateau between the Appalachian Mountains and coastal plain). Rolling greens hills and golden hay bales will greet you as you pull into pastoral Little Washington.

Hike: 4.2 mi +1500 ft

Optional Hike: 3.7 mi +/-1200 ft

Overnight: Little Washington

Day 6: Hike Whiteoak Lower Falls; Visit Copper Fox Distillery

Little Washington may lure you into a day of total relaxation, with its art galleries, spa, and three star Michelin restaurant (reservations required). But if you still have the energy and spirit of adventure, a short drive off the beaten path will take you through Sperryville, Etlan, and up into the hollows. Hike just two miles to the first waterfall in Whiteoak Canyon, or continue further upstream until you’ve had your fill.

You’ve earned a celebration, so stop off at the Copper Fox Distillery for a tour (free) and tasting (additional fee). In an old barn, this craft distillery makes unique hand-malted and fruitwood-aged spirits.

Hike: 2.8 mi +/-450 f

Overnight: Little Washington

Day 7: Onward Travel

Just over an hour’s drive separates Little Washington from Charlottesville. Don’t hesitate to ask us for advice on your onward travel plans.


Stay six nights in upscale accommodations, including two nights at boutique inns in Charlottesville and Washington, Virginia, and two nights at a lodge within the National Park. Although your accommodations will vary, all provide unique character, excellent service, and a warm welcome.

Single Rooms

This trip is based on two people sharing a room. If you’d like separate rooms, a single supplement is required. If you would like to request a twin room (same room with two separate beds), please notify us during booking so we can request this option; this may not be available in all locations.

If you would like to book this tour as a solo traveler, a solo supplement is required.


All breakfasts are included on this tour. These will vary depending on your night’s lodging but may include a selection of dishes or a continental buffet, as well as coffee and beverages. You are free to select your own lunches, snacks, and dinners, and you will see information about where to find food and drink in your route notes. You may consider packing a picnic lunch to eat during your hikes, unless you plan to arrive at your destination early in the day. The National Park lodges offer a hiker’s lunch to go (for a fee); simply ask at the reception.
When in Charlottesville, enjoy the opportunity to sample the many outstanding restaurants serving international, southern-style, and farm-to-fork cuisine.
During your stay in Little Washington, dining options are more spread out, and some involve a quick drive; alternately, opt to splurge for a meal at the Michelin-rated Inn at Little Washington (advance reservations required).

Extra Nights

You may opt to add extras nights during this itinerary as there is plenty more to see, do, and hike. For further details and pricing, please ask us at the time of booking.




Oakhurst Inn

Oakhurst Inn

This boutique hotel perfectly walks the line between personality and privacy, allowing you to fully relax in stylish rooms, just steps from their contemporary café.







Skyland Lodge

Built as an exclusive resort overlooking the Shenandoah Valley and designed as a place of relaxation and recreation, Skyland has gracefully blended modern upgrades into this historic property while holding onto the nostalgic feel of a summer camp.




These are two examples of lodging options in Little Washington; exact booking will be based on availability.




Gay Street Inn

Gay Street Inn

Quaint and cozy meet indulgent and restorative at this five-room B&B, where innkeepers Drew and Deb serve gourmet three-course breakfasts.







White Moose Inn

White Moose Inn

An 1830s building renovated for the contemporary traveler, everything about this five-room inn feels chic and modern, but you’ll still be greeted like family.







The Inn at Little Washington

Optional Upgrade – The Inn at Little Washington

On location at Patrick O’Connell’s legendary restaurant, recent recipient of three Michelin stars, ‘the inn’, as it’s referred to locally, offers history and luxury, including a guaranteed dinner reservation.





This trip is available early May through the end of October. We suggest booking as far in advance as possible for a better chance at securing your dates. This tour is available to start any day of the week.

When To Go?

Charlottesville’s weather is influenced by the mountains to the west and the Atlantic Ocean to the east; the result is a moderate climate along the Virginia Piedmont. In the shoulder months of May and September, temperatures in Charlottesville range from the mid 50s to mid 70s Fahrenheit, with October being slightly cooler. The hottest months, June through August, see temperatures as high as the 90s Fahrenheit. Temperatures in Shenandoah National Park are cooler, often up to 10 degrees Fahrenheit lower than the city, which can be a welcome respite during the summer. Overall precipitation is above the national average in the summer months, but even when it is not raining, this region of the US is known for its humidity.

Spring provides wildflowers and waterfalls galore, making it a great time to visit. Summertime is busy with vacationers and the humidity can make it a challenging hiking season, yet it beckons hikers with long days and lush green landscapes. Fall is the most popular time to visit due to the brilliant colors of the fall foliage; beware of crowds on fall weekends and try to plan your trip midweek. Peak foliage dates change quite a bit from year to year, based on precipitation and temperature.


Navigating is easy using the Macs Adventure Navigation App. Your daily hikes and drives will be mapped in the app with GPX tracks, route notes, and turn-by-turn directions. All of these resources are available to download for offline use, which is important as cell phone and Wi-Fi service are not reliable for parts of this tour. You will also have 24/7 telephone support from us here at Macs Adventure. 

You may consider using GPS navigation for your drives; however, we recommend double checking with your route notes as we have carefully selected some routes.

Experience, Fitness & Grade

The hiking on this trip is easy to moderate, averaging 4-6 miles per day. All of the hikes are optional since you will be driving yourself to the start/end point of each one. The daily hikes are suitable for a regularly active person, and none require a full day of hiking. For those guests looking for more hiking, we recommend adding the optional hikes as well (each of these can be accomplished in an afternoon). Many hikes in Shenandoah descend from Skyline Drive, meaning that you should save energy for the ascent back to your car. Trails are generally even, but sections may be rocky, muddy, rooted, and slippery (particularly near waterfalls). Due to the access from Skyline Drive, you will never be more than a few miles from the road.


Our pre-departure information pack includes a detailed equipment list on what to take with you. This includes warm and cold weather gear, hiking boots, rain gear, and lots of other specifics. If you have any questions about what to take, we'd be happy to share our own top tips and advice.

Getting Around

A rental car is required for this trip. You may coordinate this independently, or inquire with your Destination & Adventure Specialist about including it as an add-on.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

Getting to & from Charlottesville

The easiest way to get here is to fly into and out of Charlottesville Albemarle Airport.

Alternatively, you may opt to fly into Washington DC and drive (2 hours), take the train (Amtrak Crescent or Northeast, ~2.5 hours), or bus (Megabus, ~2.5 hours).


  • 6 nights in lodges & boutique inns
  • 6 Breakfasts
  • Admission to Monticello
  • Detailed pre-departure information pack
  • Turn-by turn route notes
  • Macs Adventure Navigation App for mobile phone
  • 24/7 telephone support
  • Donation to Potomac Appalachian Trail Club


  • Travel to/from Charlottesville
  • Lunches, snacks, dinners, and drinks
  • Personal equipment
  • Travel Insurance


  • Additional nights before, during, or after your trip
  • Single room or solo supplement (if required)
  • Car rental

What happens if I can’t walk a stage?

All of your hikes are optional due to the drive & hike format of the trip. You will be driving to each start/end point so you can also shorten your hikes by turning around early. You will also have the option to do some additional hikes on some days if you would like to add more mileage. This tour offers plenty of flexibility.

How far in advance do I need to book?

We suggest you book as soon as your plans are finalized as this destination is popular in the summer and autumn months. Please note you can start this tour on any day of the week, but availability is more limited on weekends.

What personal equipment do I need?

You will need good hiking shoes/boots, comfortable walking clothes (non-cotton is advised), waterproof raingear, a daypack, and warm layers. We supply a detailed packing list with your information pack.

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lf you require more information before booking, please contact us on

+44 (0)141 530 5464

+1 -844-858-0740


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Macs Adventure - Head Office: Skypark 5, 45 Finnieston Street, Glasgow, G3 8JU, UK


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