Helmets & Harvest - Eastern MD Pass

Expiration: Nov 15th 2026

Get ready for fun fall adventures with Helmets & Harvest - Eastern MD Pass from Maryland's Best.

Earn rewards, discover local favorites, and enjoy a playful blend of helmet-worthy thrills and harvest-time fun. Sign up now to secure your pass, plan your visit, and start checking in for a memorable Eastern Maryland experience with Maryland's Best.


Included Venues

See locations on an interactive map.

Chesapeake Manor Vineyard & Winery
Cross Island Trail

Enjoy the Cross Island Trail! This tree-lined linear park offers a safe avenue for non-vehicular transportation. The trail is 6.5 miles long, spanning east to west from Terrapin Park to the Chesapeake Heritage and Visitor Center at Kent Narrows, and beyond to Long Point Park in Grasonville.

The trail wanders through farmlands, meadows and woods accented with ornamental trees. Flanked by park benches, the trail crosses several creeks with wooden bridges, offering a spectacular view of waterfowl and wetlands.

Portable toilets are available year round. You can also park at Old Love Point Park at 300 Old Love Point Rd, Stevensville, MD 21666 or Terrapin Nature Park at 191 Log Canoe Cir, Stevensville, MD 21666.

Need a bike rental? Fin bike rentals are available near the Holiday Inn in Kent Narrows N and near the Waterman's Monument across the street of Kent Narrow Way S.

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Ten Eyck Brewing Company
Councell Farms
Councell Farms is a family-owned agricultural operation nestled at 11773 Old Skipton Rd in Cordova, Maryland. Nestled along the rural countryside, the farm offers a welcoming, small-town atmosphere rooted in generations of farming tradition. Visitors can expect a warm rural experience, seasonal produce, and a glimpse into the farm’s enduring commitment to sustainable practices and community-focused farming.
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Easton Rails to Trails

The Easton Rails-to-Trails runs is nearly 3 miles, spanning the majority of Easton running north to south. The trail opened in 1998 and has been a popular spot for walking, jogging, biking, and sightseeing.

The trail runs right through Easton and provides great access local stores, parks, destinations, and schools. The original railroad station (converted into Town of Easton offices) is near the midpoint of the trail near Goldsborough Street.

Parking for the Easton Rails to Trails can be found in Idlewild Park (115 Idlewild Ave). Bike or walk two blocks east from the park to access the trail. Parking is also available on Springdale Avenue next to the Board of Education building (12 Magnolia Street), the North Easton Sports Complex (1078 N Washington St), Train Station (46 Pennsylvania Avenue) and Moton Park (501 Port Street). Restrooms located in North Easton Sports Complex, John Ford Park, Idlewild Park and Moton Park. Drinking fountains located on the Rail Trail in several locations.

Need a bike rental? Check out Easton Cycle & Sport at 723 Goldsborough St, Easton, MD 21601.

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St. Michael's Winery
St. Michael's Winery, nestled along the charming waterfront of St. Michaels, Maryland, invites guests to sip locally crafted wines in a welcoming, rustic setting. Located at 609 S Talbot St, this family-owned winery blends maritime charm with winemaking tradition, offering a curated lineup that highlights Maryland’s terroir and the region’s storied coastal character. Whether you're sampling a crisp white or a velvety red, the intimate tasting room atmosphere and scenic harbor views make for a delightful, relaxed experience.
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Terrapin Run Recreation Trail

The Terrapin Run Recreation Trail is located in Somerset County, Maryland. The trail is 12 miles point-to-point. The trail parallels State Route 413, and is built in the former railbed of a railroad that went bankrupt in the mid-70s. The trail is flat, shaded in some parts and exposed in others, so keep that in mind when visiting in the hotter months. Benches on the path provide respite for tired trail users.
Additional trailheads and parking available at Trailheads are at 28242 Hinman Lane in Marion and 4053 Hinman Lane in Crisfield.
Need a bike rental? Bikes are available to rent at Janes Island State Park for campers and limited bikes are available at Somers Cove Marina.

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Sugar Water
Sugar Water is a Farm and Water to Table restaurant in the Washington Hotel in Princess Anne. Focused on serving fresh local food simply. The food is delicious, tells a story and community gathers.
Ben Cardin C&D Canal Trail

Maryland's Ben Cardin C&D Canal Recreational Trail links to Delaware's Michael Castle Trail (which extends an additional 12 miles); both run along the north bank of the Chesapeake and Delaware (C&D) Canal and meet at the state line. The combined route takes travelers from the historical, quaint canal town of Chesapeake City to Delaware City.

The closest bathroom in Chesapeake City is at Helen Titter Park, a short walk from the trailhead, or up Lewis Street, crossing Biddle St and following the alley around to the park.

Need bikes? Find rentals near the starting location, Fin Bike Rentals.

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Dove Valley Vineyard
Milburn Orchards
Milburn Orchards, nestled at 1495 Appleton Rd in Elkton, MD, is a family-owned destination offering seasonal U-pick apples, fresh-baked pies, doughnuts, and farm-fresh goodies. With welcoming grounds for picnics, a charming country store, and friendly hospitality, it’s a quintessential Maryland orchard experience for locals and visitors alike.
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Assateague Island Bike Path

Hop on your bike and explore the island!

Cyclists may travel to Assateague over a bicycle-pedestrian bridge and follow a paved bike path along Bayberry Drive through 4 miles of island habitat. There is a parking lot for hikers and cyclists on the southwest side of the bridge to Assateague as well as parking on Assateague Island. Parking is free at the Visitor Center lot. Restrooms are near the Visitor Center. There is no entrance fee for the National Seashore when entering by bike. Dogs are allowed.

Need a bike rental? Rental bikes are available seasonally from Assateague Outfitters, with stands located at the Visitor's Center and at the end of Bayside Drive inside the National Seashore. Check AO's website for up-to-date hours and information.

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Twin Oak Farms
Twin Oak Farms at 1128 Snow Hill Rd in Stockton, Maryland, is a serene rural retreat nestled in the heart of the Eastern Shore. This family-owned property blends picturesque farmland with homegrown hospitality, offering fresh produce, locally sourced goods, and a welcoming atmosphere for visitors and neighbors alike. Explore rolling fields, charming farmstead views, and a commitment to sustainable farming that honors the land and community.
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Blacksmith Restaurant Berlin