Bicycling and Walking Vacations Since 1971 Call a VBT Tour Consultant: (800) 245-3868

Maryland: Cycling the Chesapeake Bay

The lure of the sea tugs deep into the soul of Chesapeake Bay, a rising tide of maritime tradition, close-knit communities, protected seashores, marshes, and coastal islands, and regional cuisine as distinctively flavorful as any in the world.

  • Activity Level: Easy
  • Daily Mileage: 13 - 32 mi
  • Daily Biking: 2 - 4 1/2 hr
  • Small Groups: 20
  • Biking
  • Easy

Why You'll Love This Tour

Overview

Maryland: Cycling the Chesapeake Bay

The towns and villages of Maryland’s bay region have given rise to generations of devoted and creative shellfishermen, craftspeople, and culinary artisans who will welcome us like family. From elegant 18th-century brick mansions to weathered crab shacks by tidal ponds, we’ll feel the warm glow of daily life as only possible on bike and on foot, on an active vacation that features the most welcoming bicycling landscape of any in the country.

Cultural Highlights

  • Sail the eastern shores with Captain Ed onboard the skipjack HM Krentz
  • Feast on the region's famous crab and seafood
  • Be entertained during an evening of local storytelling and music
  • Amble the wooden boardwalk at the Eastern Neck National Wildlife Refuge, a haven for more than 240 bird species
  • Browse the restored crab shacks, now artisans' shops, in Rock Hall – “where nice people live”
  • Engage with history past and present at a working boatyard at the Chesapeake Bay Maritime Museum

What to Expect

This tour offers options for easy rides throughout the trip. The terrain includes very few gradual hills. It’s possible to ride this entire week without the need for van shuttles. However, our VBT van support shuttle is always available in cases of inclement weather or for those who wish to shorten their rides.

What’s Included:

  • 5 nights in historic inns
  • 11 meals – 5 breakfasts, 3 lunches, 3 dinners
  • FREE use of our custom VBT bicycle and helmet
  • Service of two VBT Trip Leaders
  • FULL VAN SUPPORT
  • Daily route directions and maps
  • Welcome reception
  • Sightseeing and cultural activities
  • Transfers
  • 5% Frequent Traveler Credit to use on your next VBT vacation
  • Special Good Buy Discount
Dates & Prices

Departure &
Return Dates

Now Showing:

Land Only

Air Not Included,
Departs after Air Package Plus.
April
Sun, Apr 19
to Fri, Apr 24
Departure: Sunday, April 19
Return: Friday, April 24
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
Sun, Apr 26
to Fri, May 1
Departure: Sunday, April 26
Return: Friday, May 1
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
May
Sun, May 3
to Fri, May 8
Departure: Sunday, May 3
Return: Friday, May 8
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
Sun, May 10
to Fri, May 15
Departure: Sunday, May 10
Return: Friday, May 15
Close
From $2,345
  • From $2,345
  • (800) 245-3868
Close
Sun, May 17
to Fri, May 22
Departure: Sunday, May 17
Return: Friday, May 22
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
June
Sun, Jun 7
to Fri, Jun 12
Departure: Sunday, June 7
Return: Friday, June 12
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
September
Sun, Sep 6
to Fri, Sep 11
Departure: Sunday, September 6
Return: Friday, September 11
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
Sun, Sep 13
to Fri, Sep 18
Departure: Sunday, September 13
Return: Friday, September 18
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
Sun, Sep 20
to Fri, Sep 25
Departure: Sunday, September 20
Return: Friday, September 25
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
Sun, Sep 27
to Fri, Oct 2
Departure: Sunday, September 27
Return: Friday, October 2
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
October
Sun, Oct 11
to Fri, Oct 16
Departure: Sunday, October 11
Return: Friday, October 16
Close
From $2,045
  • From $2,045
  • (800) 245-3868
Close
Sun, Oct 18
to Fri, Oct 23
Departure: Sunday, October 18
Return: Friday, October 23
Close
From $1,995
  • From $1,995
  • (800) 245-3868
Close

Land Only Single Supplement: $395

Please note: Web Special savings cannot be combined with any other offer. Standard Terms & Conditions apply when purchasing this trip. 2015 Prices include all airline surcharges and Government taxes and fees. Ask our Tour Consultants for details. Every effort has been made to produce this information accurately. We reserve the right to correct errors. Prices are based on preferences selected above, including meals and sightseeing as specified in What's Included. All prices are subject to change. Departure dates and prices shown may be updated several times daily, and apply to new bookings only.

Itinerary & Map
Or, Expand All Days
DAY 1: Arrive Easton / Warm-up ride / Welcome reception

Make your own arrangements for travel to Maryland. If you're flying to Baltimore, VBT will offer a shuttle from the Baltimore-Washington International Airport (BWI). The shuttle works on a “show and go” basis and will make its only departure from the airport to the inn at 1:00 pm. Shuttle reservations are not required or available. The shuttle will depart from the lower level, the baggage claim level, at Door 10 on the inner roadway. Your shuttle bus will carry “GO The Airport Shuttle” titles, and the driver will be holding a VBT sign.

If you are scheduled to arrive at the airport after 1:00 pm or are delayed, you must take a taxi or bus at your own expense. If you are driving to the tour, we recommend that you leave your vehicle in Easton while on tour. You can park at the Tidewater Inn while on tour (Sunday through Thursday nights inclusive). You may return to this location at the end of the tour by way of the VBT van.

If you are delayed or your travel plans change, please contact the first inn; they will pass your message to your VBT Trip Leaders.

Our group meets at the Tidewater Inn to begin your Maryland vacation. After settling in, explore the village from the hotel's central location. At 3:00 pm, join your VBT Trip Leaders for a safety and bike-fitting session, followed by a short warm-up ride. At 5:00 pm, meet up with the group for an orientation and welcome reception before a 7:00 pm dinner at the inn.

DAY 2: Ride the Oxford & St. Michaels Trail / Lunch in St. Michaels / Guided visit to the Chesapeake Bay Maritime Museum

Today you are in for a treat. The Oxford/St. Michaels loop is considered one of the premiere biking routes on the east coast. We ride a counter-clockwise route from our inn, stopping for an included lunch in St. Michaels, a small bayside town on a long, narrow neck of land. Afterward, our group will have a self-guided tour of the impressive Chesapeake Bay Maritime Museum. The museum comprises more than ten exhibit buildings, the 1879 Hooper Strait Lighthouse, a working boatyard and the world's largest collection of Bay boats. Plus, St. Michaels offers wonderful shopping, snacking and plenty of people watching opportunities.

After our visit in St. Michaels, we’ll hop back on our bikes, riding through Royal Oak to reach Bellevue. Upon arrival, we'll board the modest Oxford-Bellevue ferry, the oldest privately owned ferry still in operation in America. After crossing, we'll be in Oxford. Worth a stop, this 17th-century town has a long tradition of boat building. Don't forget to stop for homemade ice cream! The Scottish Highland Creamery is the place for it.

After your mid-afternoon ice cream delight, continue back to our inn. Easton has been featured on many “best small towns in America” lists. The village is small in scale, but packed with great dining, antiques, galleries and shopping. Our comfortable inn has played a central role in the village since 1712. Recently renovated, it features great eating and drinking at Hunters' Tavern.

For dinner, choose from one of the fine restaurants in town.

DAY 3: Ride the farmlands of Talbot County / Cordova / Dairy visit and hand-crafted cheese tasting

More than half of the land in Talbot County is devoted to farming and we’ll spend the morning riding through its wide-open agricultural terrain.
We divert from the rows of wheat, corn and soybeans, riding on shaded lanes leading down to rewarding views of the Choptank River. Stop at Kingston Landing for a relaxing respite. The river’s edge is an active birding area and you may spot Bald Eagles, Yellow-throated Warblers or Indigo Buntings.

Later, we’ll ride on to the sleepy town of Cordova. You might enjoy exploring the town’s two general stores before we turn west, riding back towards Easton. En route to our inn, we’ll stop for a picnic lunch on the grounds of a family run farm. After our picnic, we’ll meet Eric and Holly and their grass-fed girls for an introduction into the dairy operation at work. Before hitting the road, we sample the artisanal cheeses and other products made here at Chapel’s Country Creamery.

Tonight's dinner is at one of Easton's popular restaurants.

DAY 4: Sail to Rock Hall / Eastern Neck Island National Wildlife Refuge

This morning, board the HM Krentz for a sail north through the Kent Narrows to Rock Hall. Our skipper, Captain Ed, has spent more than 35 years dredging oysters and sailing skipjacks for his livelihood and his boat, the HM Krentz, is a broad-beamed former working skipjack. Her stable decks are perfect for catching sea air.

On arrival in Rock Hall, we'll enjoy a picnic lunch before cycling to the Eastern Neck Wildlife Refuge. A glorious haven for more than 240 bird species, you might want to take a walk along the wooden Tubby Cove Boardwalk, which extends over the marsh to a wooded island. Once on the island, the boardwalk continues to two viewing platforms, and a rough walking trail off the main path ends at an elevated viewing platform that provides vistas of Chesapeake Bay and into Tubby Cove and Calf Pasture Cove. After exploring, we'll continue our ride to the inn, where a swim in the pool and a cool drink on the dock may be in order. Our hosts Jim and Joanne welcome us. Dinner is on your own tonight in one of Rock Hall's restaurants.

DAY 5: Ride to Chestertown

We ride north today to Chestertown, an historic colonial town located on the Chester River. Chestertown was founded in 1705, and became one of Maryland's six Royal Ports of Entry, and in the mid-eighteenth century it was the second leading port in Maryland. With this important designation and the resulting shipping business, the town became quite wealthy, as heralded by the brick mansions and townhouses along the waterfront. Your leaders will offer you a self-guided cycling tour of the historic section of Chestertown.

Continue exploring along the town's brick sidewalks, visiting shops and galleries along the way. While you're in Chestertown, take the time to enjoy lunch on your own at a local cafe, the bakery or one of the town's numerous restaurants. Your leaders will provide you with some great recommendations.

If you prefer a non-riding option today, you may spend the day at the inn, or enjoy browsing the charming shops and relaxing in the cafes in Rock Hall.

Tonight, we gather to celebrate with a festive farewell dinner.

DAY 6: Depart for home

Our tour concludes after breakfast at our inn. Our included shuttle is available to take you back to the Baltimore-Washington International Airport (BWI), arriving around 12:00 pm. We suggest a flight out of BWI no earlier than 2:00 pm. We will shuttle guests who have cars parked at the Tidewater Inn. This shuttle will arrive at the inn around 12:00 pm.

Download Itinerary PDF

Download Now
Accommodations

Inn at Hungtington Field Creek

The Inn at Huntingfield Creek is a 70-acre refuge in the finest Chesapeake tradition. Hosts Jim and Joanne Rich each bring business and life experiences together to create wonderful memories at this quiet, country retreat. Our group will have exclusive use of the inn during our stays. Enjoy the swimming pool, the piano in the living room, and the sunset views from the dock over the tidal waterfront. This is the perfect setting from which to venture out on our planned activities.
Free WiFi Included

Tidewater Inn

Accommodations at the Tidewater Inn offer the best of both worlds: the tranquility and charm of a historic Colonial inn along with the modern luxuries today’s traveler has come to expect. Traditional decor and furnishings offer the perfect reflection of our historic downtown Easton setting, while resort-style amenities make for an indulgent stay. Relax in plush bedding featuring pillow-top mattresses under a cascade of fine European linens. Wrap yourself in a downy Egyptian cotton robe. Enjoy tech-savvy touches like flat-screen televisions and high-speed Internet access.
Free WiFi Included
Photos

Reviews
  • Superb Guides As Always

    The Chesapeake Bay trip is another VBT winner, though I think you get more value for your money overall on the international trips. The strength of the trip, as always, was the quality of the guides. Valerie and Mark were excellent and always willing to assist and accommodate in every way. Most of the bike rides were quite good, but the morning ride of the first day was not enjoyable, in that there was far too much traffic and no shoulder on some roads. Perhaps there was no decent alternative. The countryside was scenic and I always appreciate the non-biking extras that VBT includes to get a better feel of the region, including a boat ride, tour of a working dairy farm and folk singer.

    Yes, I recommend this tour.

    Posted on: June 05, 2014
    Posted by: Kip22
    From: Bensalem, PA 19020, USA
    Age: 45 to 54
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • Another great VBT trip!

    We had a lovely time exploring the Chesapeake Bay Area. The rides were easy with flat terrain. We were able to ride on back roads with little traffic and were fortunate to have mostly good weather. The side trip on a skipjack happened on a cooler day bug was still fun. The visit to a creamery was excellent. We were with a wonderful group of people and our guides, Valerie and Mark, were terrific

    Yes, I recommend this tour.

    Posted on: May 20, 2014
    Posted by: Joannkv
    From: Denver, CO, USA
    Age: 55 to 64
    # Of Trips: 2-4

    • Value:
    • Trip Leaders:
  • Great tour for first-timers

    We had never done bicycle touring, so this trip looked like a good introduction, and it was superb. The leaders were exceptional in providing coaching and support as well as all the daily logistics needed. The additional activities--trip on a skipjack, visit to a creamery, cycling through a nature preserve, to mention just a few--were all excellent. The inns chosen were elegant and comfortable. The food was delicious and the surroundings just beautiful. We came home eager to book our next tour.

    Yes, I recommend this tour.

    Posted on: May 05, 2014
    Posted by: Katharine
    From: New Jersey
    Age: 55 to 64
    # Of Trips: 1

    • Value:
    • Trip Leaders:
  • An interesting place to explore in the US

    We wanted an East Coast US tour. This trip allowed us to enjoy the beauty of Maryland's Eastern shore. On a bicycle trip I expect great local food and color. We were not disappointed. From our introductory maintenance clinic to our skipjack tour of the Chesapeake every activity was conducted by experts. Thanks to Chapel's Country Creamery I have a greater appreciation of what it means to be a small farmer and cheese maker.

    Yes, I recommend this tour.

    Posted on: November 12, 2013
    Posted by: Wendy
    From: St. Louis, MO, USA
    Age: 55 to 64
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • Great location, great tour guides, great equipment, great friends - who could ask for anything more!

    This was our first VBT experience, but it will surely not be our last. We've already booked another trip. This is a well organized trip, with knowledgeable and friendly guides. No peer pressure - you can ride with others or by yourselves. The guides on bikes and in the van make sure no one is left behind. Reasonable mileage between rest stops with energy snacks always available. The routes are well planned, safe, and easy to follow directions are mounted on your bike. Fun things to see throughout the trip. Great accommodations. We highly recommend the VBT experience!

    Yes, I recommend this tour.

    Posted on: June 02, 2013
    Posted by: DoubleB
    From: Plantation, FL, USA
    Age: 55 to 64
    # Of Trips: 1

    • Value:
    • Trip Leaders:
  • This tour was perfect for "easy" riders.

    We've done many VBT tours over the years and this one fit us perfectly. The accommodations, itinerary, pace, and leaders made us so happy, we have already signed up for another trip.

    Yes, I recommend this tour.

    Posted on: December 06, 2012
    Posted by: DLK4
    From: Western PA
    Age: 65 or over
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • a relaxing slow paced trip!

    we so enjoyed this trip in the fall as the leaves were beautiful, the migratory birds in abundance, the pace of riding very relaxed. i advise anyone interested in experiencing the Chesapeake Bay area to join in on this VBT tour. as always the guides and Inns were of the high standard of VBT vacations! we throughly enjoyed this vacation!

    Yes, I recommend this tour.

    Posted on: November 15, 2012
    Posted by: bugsterry
    From: haw river, nc
    Age: 45 to 54
    # Of Trips: 2-4

    • Value:
    • Trip Leaders:
  • Loved the afternoon on the water!

    A lovely part of the country to see on a bicycle, especially VBT style. Lots of variety - the waterways, small towns and farmland. Easy riding but there is a pretty constant head wind that doesn't ever completely go away. I've been on several VBT trips and this one was great like the others except tour leaders did not meet previous VBT standard of excellence.

    Yes, I recommend this tour.

    Posted on: November 14, 2012
    Posted by: JSusan
    From: Texas
    Age: 55 to 64
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • The Chesapeake Bay area is an undiscovered gem and the best way to absorb it is on a bicycle.

    As a 1st time VBT guest, we loved the experience. The 30 mile per day rides were a breeze as the area is flat. There was minimal traffic with which to contend. The accommodations & regional food were a big plus. The rides were pleasantly integrated with a ferry ride, a visit with a docent @ the maritime museum, an architectural tour of colonial buildings & visiting a small family run dairy farm where they made fabulous artisanal cheeses. The scenery is sublime. The guides were upbeat & fun. Every guest was friendly & inclusive.

    Yes, I recommend this tour.

    Posted on: October 25, 2012
    Posted by: Donna52
    From: San Diego, CA, USA
    Age: 55 to 64
    # Of Trips: 1

    • Value:
    • Trip Leaders:
  • Nice, relaxing US trip

    This year I needed a shorter, less expensive trip than I usually take with VBT, so I chose this one. It was a great choice, and I was rewarded by spectacular weather every day. There was relatively little in-town biking or busy road routes, and some spectacular rural biking--most of it nice and flat! The hotel stays were good, too, especially the second one further away from civilization. The 'side' trips were excellent, especially the trip on the Chesapeake Bay on the Skipjack working boat.

    Yes, I recommend this tour.

    Posted on: October 23, 2012
    Posted by: 60sLibrarian
    From: Jacksonville, NY
    Age: 55 to 64
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • Beautiful scenery, easy trails and superb hotels!

    This was one of our favorites so far...and we have been on quite a few of VBT's trips. The small towns, wonderful restaurants and easy, breezy bike trails were more that expected. The 2 hotels were quaint and yet had all the ammenities to make you comfortable. Only staying at 2 places was nice, as there was not too much packing and moving. I would stay at the Tidewater Inn and The Inn at Huntingfield again in a heartbeat. This is a trip that I would highly recomend to anyone who wants all the above, exercise, beautiful outdoors and towns and no worries other than the decisions on what wonderful food to eat.

    Yes, I recommend this tour.

    Posted on: October 18, 2012
    Posted by: Mema5
    From: Denver, CO, USA
    Age: 55 to 64
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • A good trip for older people.

    The tour was a good experience, in a part of the country I had never seen before. It is not a dramatically scenic area. but very plesant and easy for older people like myself to handle. We enjoyed the visit to the dairy, the skipjack boat ride, and the Rock Hall bed and breakfast particularily. I had started but not finished the novel Chesapeake and was sorry I had not done so before the trip.

    Yes, I recommend this tour.

    Posted on: October 13, 2012
    Posted by: Will
    From: Honolulu, HI, USA
    Age: 65 or over
    # Of Trips: 2-4

    • Value:
    • Trip Leaders:
  • This tour is a winner.

    The rides were wonderful, relaxing. I especially enjoyed the quiet backroads, farmlands and small towns. The inns were great, the food excellent, and above all, the two tour leaders were the best. They were extremely knowledgeable about the area, bike mechanics, very helpful, very personable and couldn't have asked for more. Thanks for adding this tour!

    Yes, I recommend this tour.

    Posted on: July 25, 2012
    Posted by: Jazz
    From: New York, NY
    Age: 65 or over
    # Of Trips: 2-4

    • Value:
    • Trip Leaders:
  • Great to see and learn more of America. Loved the history and beauty of the Chesapeake.

    This is a wonderful area of the East Coast. The tour of a dairy farm was one of the highlights. Tours of this sort can be"ho hum" or "been there, seen that". But we really had fun meeting the delightful owner of a beautiful organic dairy and tasting the terrific cheeses that were being produced there. It was also great to cycle beautifiul countryside punctuated with small, historic towns fjilled with early American history. A trip on a skipjack left us with much more knowledge and appreciation of oyster farming and those that harvest these endangered bivalves. Oysters on the half shell will never be looked at the same! The last nights entertainment was great -- an extremely talented and historically knowledgeable banjo player made the music of the area and its peoples come alive. Plus, we ate great food!

    Yes, I recommend this tour.

    Posted on: July 08, 2012
    Posted by: Momo
    From: San Francisco, CA, USA
    Age: 65 or over
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • This trip was very educational

    This was a great trip - lots of country roads to ride and we got a real flavor for the area. I had never even heard the word Delmarva but certainly know about it now. The accommodations were up to VBT standards as was the food and of course the wonderful guides.

    Yes, I recommend this tour.

    Posted on: July 06, 2012
    Posted by: Sarah
    From: Edmond, OK, USA
    Age: 55 to 64
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • This tour was a deligtful treat for the spring...

    For me the degree of difficulty and flexibility in this trip was perfect. The scenery was beautiful, the accomodations, superb & the mix of biking,boating, & visiting interesting sites was invigorating and relaxing at the same time. Of course, as usual, the people were congenial & the tour guides, fantastic!

    Yes, I recommend this tour.

    Posted on: July 06, 2012
    Posted by: Nonna
    From: Altoona, PA
    Age: 65 or over
    # Of Trips: 5 or more

    • Value:
    • Trip Leaders:
  • Excellent biking and additonal activities

    Great tour with great leaders. Beautiful countryside

    Yes, I recommend this tour.

    Posted on: June 26, 2012
    Posted by: Divnmania
    From: Gulf Breeze, Fl
    Age: 55 to 64
    # Of Trips: 2-4

    • Value:
    • Trip Leaders:

Get The Most Value With VBT

Travel Protection Plan

  • VBT takes pride in making sure every step is taken to ensure your perfect vacation, but unexpected events can arise.
  • Our exclusive Preferred Vacation Protection Plan provides extra peace of mind.
  • What could be more precious to protect than you and your loved ones?

Air Advantage

Secure, easy, pay at your own pace...
VBT is committed to providing unsurpassed value to our travelers, including airfare. Fly aboard world-class airlines, enjoy extended stays, and even choose your departure times and routes with Customized Air and save even more on your vacation.

Good Buy Plan

Save even more...
Reserve early, lock in your low cost and save! Your dream vacation is within your reach when you take advantage of our discounts for paying in advance. The earlier you pay, the better you save.

Talk To A
VBT Tour Consultant

(800) 245-3868

  • Mon – Fri 8:30am – 6:30pm EST
  • Saturday 10:00am – 3:00pm EST

Related Tours You Might Be Interested In

vermont-champlain-valley-2015---lead

Vermont: Champlain Valley & Islands

From only $1,645
Discover the unspoiled beauty of northwest Vermont’s island paradise at a pace that reflects its rural way of life.

6 Days
Take Me There
classic-vermont_2015_Lead

Classic Vermont

From only $1,645
We invite you to discover the country roads, gentle mountains, quaint villages, hardwood forests, picture-perfect lakes, and strong community values that exemplify our beautiful home—Vermont’s pastoral Addison County.

6 Days
Take Me There
Cape-Cod-2015---Lead

Cape Cod & Martha’s Vineyard

From only $2,145
Shaped like an arm in a welcoming embrace, Cape Cod retains much of the maritime charm and weathered-shingle ambiance of its long-gone whaling days, when the Massachusetts coast and the island of Martha’s Vineyard were bustling economic engines.

6 Days
Take Me There
Xanterra

© 2014 VBT. All Rights Reserved.
VBT Bicycling and Walking Vacations, 614 Monkton Rd., Bristol, Vermont 05443-0711
Talk to a VBT Tour Consultant: (800) 245-3868