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Maryland Biking Tours

RIVER GORGES | TRAIL TOWNS | BIG HISTORY

WHY MARYLAND?

Follow one of the East Coast’s great long-distance riding experiences on a Maryland bike tour

Experience the GAP and C&O Canal Trail. These are trips filled with rail-trail miles, canal history, river scenery, and the quiet satisfaction of traveling through changing landscapes one day at a time.

If you’re looking for guided Maryland bike tours or a supported trail ride that blends history, scenery, and easy logistics, this is a wonderful fit. You can focus on the ride while everything else is thoughtfully handled.

MARYLAND TOURS

Guided Bike Tours in Maryland

Follow the trail and explore our Maryland bike tours along the iconic GAP and C&O Canal.

7-Day GAP & C&O Canal Trail Historical Bike Tour

4.7/5

7-Day GAP & C&O Canal Trail Historical Bike Tour

  • 7 days
  • Level 2
  • fromUSD 3,699/pp incl. taxes & fees

Explore the GAP and C&O Canal trails on a 7-day historical bike tour from Pennsylvania to Washington, D.C., with riverside paths, canal history, and relaxed riding.

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4-Day GAP Trail Getaway Rails-to-Trails Bike Tour

4.5/5

4-Day GAP Trail Getaway Rails-to-Trails Bike Tour

  • 4 days
  • Level 1
  • fromUSD 2,499/pp incl. taxes & fees

Pedal the Great Allegheny Passage on a 4-day rails-to-trails getaway. Smooth surfaces, riverside scenery, and stress-free support along the way.

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WHAT MAKES IDAHO SPECIAL

Three Trails. One Extraordinary Week.

Idaho delivers the kind of riding that stays with you long after you're home. Here's what you can look forward to.

The Route of the Hiawatha

The Route of the Hiawatha

A bucket-list rail trail experience — dramatic trestles, cool mountain tunnels, and sweeping views through the Bitterroot Mountains. It's the kind of ride people talk about for years.

Trail of the Coeur d'Alenes

Trail of the Coeur d'Alenes

Glide along pristine lakeshores and wetlands on one of America's most celebrated rail trails. Quiet, flat, and utterly beautiful — it's perfect for soaking in the scenery at your own pace.

Unforgettable Scenery

Unforgettable Scenery

Towering forests, sparkling rivers, and open mountain skies — Idaho's wilderness is genuinely spectacular. You won't just ride through it. You'll feel completely part of it.

Frequently Asked Questions

What you need to know about cycling tours in the stunning state of Maryland.

Maryland cycling tours highlight the state’s rich history and scenic beauty. Riders can enjoy cycling along the iconic C&O Canal towpath, explore Civil War landmarks, and visit charming towns like Frederick and Annapolis. The tours often feature picturesque riverside trails and views of the Chesapeake Bay.
Maryland offers primarily flat and well-maintained trails, such as the C&O Canal towpath. Some routes may include gentle rolling hills, making the terrain accessible to cyclists of all levels.
The best time for cycling in Maryland is from spring to fall (April to October). During these months, the weather is mild, and the scenic routes are surrounded by blooming flowers in spring or vibrant foliage in autumn.
Maryland tours often include visits to historical sites like Antietam Battlefield, canal towns such as Harper’s Ferry, and museums that highlight the state’s Civil War and colonial history. Riders can also enjoy local cuisine, including Maryland’s famous crab dishes.
Yes, Maryland cycling tours are designed to accommodate all skill levels. The flat terrain of trails like the C&O Canal makes it easy for beginners, while experienced riders can opt for longer routes to explore more of Maryland’s scenic and historical attractions.

Highlights From Our Idaho Tour

Our Riders Share Their Stories

Real guests. Real rides. Real discoveries.

From breathtaking views to lifelong friendships, find out why guests love riding with Discovery Bicycle Tours.

It was a perfect sunny day for riding north along the Hudson. The guide we had was excellent and knowledgeable. It was really a wonderful experience for me.

- Laura B

Empire State Trail Bike Tour

The tours they had prearranged were way beyond my expectations! The schedule was just perfect…we had the chance to do plenty of biking but the days weren’t too full. Will definitely look into more trips with Discovery!

- Coleen H

Natchez Trace Parkway Historical Tour

Our guides were exceptionally attentive, knowledgeable and patient. The accommodations were superb. Unquestionably a five-star cycling adventure — look no further than Discovery Bicycle Tours.

- Suzanne M

P'tit Train du Nord Quebec's Rail Trail

Why Travel With Discovery?

Riding together since 1977

Since 1977, these trips have been thoughtfully crafted to feel smooth, personal, and stress-free.

Your tour leaders bring local insight, steady support, and genuine care, handling the details so you can simply enjoy each moment and savor the journey.

Ride your way fully supported

You set the pace each day — pause for a view, stop for coffee, or keep rolling. It’s up to you.

With flexible mileage, simple Ride with GPS navigation, and a support van nearby, you can ride confidently knowing help is there if you need it.

E-Bikes Included

Every tour includes e-bikes at no extra cost.

Whether you want a little boost on the hills or simply an easier, more relaxed day in the saddle, the choice is always yours — so you can ride comfortably, confidently, and enjoy every mile at your own pace.

Scenic routes you'll love

You’ll follow thoughtfully designed routes along quiet back roads, rail trails, and car-free paths.

It’s the kind of riding where you can relax, take in the views, and really connect with each place along the way.

Small groups, lifelong friends

You’ll ride alongside a small, welcoming group where it’s easy to connect. Share meals, swap stories, and laugh about the day’s highlights.

It doesn’t take long before it feels like traveling with old friends.

All-inclusive, no surprises

From handpicked inns and most meals to quality bikes, helmets, expert tour leaders, and van support, it’s all taken care of and included.

No planning stress. No surprise costs. Just arrive, settle in, and enjoy the ride.

Popular Adventures

  • Idaho Trails Bike Tours
  • Quebec Rail Trail Tours

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Mailing Address: PO Box 700, Woodstock, VT 05091
Address: 2520 W. Woodstock Rd., Woodstock, VT 05091
(800) 257-2226

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