Helmets & Harvest - Western MD Pass

Expiration: Nov 15th 2026

Get ready for fun fall adventures with Helmets & Harvest - Western 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 Western Maryland experience with Maryland's Best.


Included Venues

See locations on an interactive map.

1812 Brewery
Great Allegheny Passage

With countless day trips imaginable and a nearly-level trail surface, the Great Allegheny Passage is the perfect spot for your next biking adventure. Every mile (150 total) offers super scenery, from vistas in Maryland’s mountains to open meadows in Pennsylvania’s Laurel Highlands. Railroad history abounds, and you’ll find remnants of the coal and steel industries on which the United States was built. In Maryland, the GAP can be accessed from Cumberland or Frostburg.

In Cumberland, we recommend starting at Canal Place, where the GAP meets the C&O Canal. Need a bike rental? Check out Wheelzup. Free overnight parking can be found off of Howard Street. Restroom Facilities are available at Canal Place Mile Marker 1.

In Frostburg, the trail can be accessed by the Old Train Depot. Need a bike rental? Check out Tracks and Yaks.

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Charis Winery & Distillery
Charis Winery & Distillery is a boutique craft destination in Cumberland, Maryland, welcoming visitors to explore small-batch wines and artisanal spirits. Nestled at 17 Howard St, the venue blends intimate winery charm with a modern distillery edge, offering tastings, scheduled tours, and a cozy, rustic atmosphere that celebrates local ingredients and handcrafted techniques. Whether you’re savoring a tasting flight or a signature cocktail, Charis invites you to discover Maryland’s growing legacy of flavorful wines and refined spirits.
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Locust Post Brewery
Locust Post Brewery sits at 31706 Old Adams Rd NE in Little Orleans, MD, a cozy craft brewery that blends rural charm with bold, flavorful beers. Visitors can expect a welcoming taproom, rotating seasonal brews, and small-batch creations inspired by the region’s history and landscape. Whether you’re stopping by for a quick pint or staying for a tasting flight, Locust Post offers a relaxing escape with approachable styles and friendly staff.
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C&O Canal Towpath - Brunswick

Many people refer to the C&O canal towpath, but what is it exactly? The towpath is the dirt and stone path that runs 184.5 miles along the C&O Canal, where visitors can walk, run, or bike the distance between Georgetown, D.C. and Cumberland, MD. It was originally built for the canal mules to walk beside the canal as they “towed” the canal boats through the waterway. Today, it is a popular recreational trail for the millions who visit each year.

If you're in Frederick, we suggest starting in Brunswick. There is plenty of free parking at the MARC Train station, which is right by the trail. The restroom in the train station is open from 4am-8pm on weekdays.

Need a bike rental? Check out Bridgeway Bikes at 5 W Potomac St, Brunswick, MD 21716.

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Jumbo's Pumpkin Patch
Jumbo's Pumpkin Patch at 6521 Holter Rd in Middletown, MD invites families to a seasonal celebration of autumn. Explore acres of pick-your-own pumpkins, gourds, and seasonal decorations, plus friendly farm animals, photo-worthy corn mazes, and fun festive activities for all ages. A cozy, rural escape, it’s the perfect spot to make lasting fall memories with friends and family.
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Black Ankle Vineyards
We strive to produce wines that express the land in which they are grown, enhance the food they accompany, and (most important of all) are a joy to drink.
Deliteful Dairy
Deliteful Dairy is a charming family-owned dairy farm nestled in the picturesque countryside of Williamsport, Maryland. Situated on 16230 Long Delite Ln, this idyllic location provides a peaceful and serene setting for visitors to enjoy a taste of farm life. At Deliteful Dairy, visitors can experience the beauty of the rolling hills and lush pastures that house the farm's beloved herd of dairy cows. The cows are well-cared for and thrive in the open fields, grazing on nutrient-rich grasses to produce the high-quality milk that Deliteful Dairy is known for. The farm offers a variety of dairy products, including fresh milk, cream, butter, and cheese, all made from the milk produced by their own cows. Visitors can purchase these products directly from the farm's charming on-site store, where they can also pick up freshly baked goods and other locally sourced items. In addition to their dairy products, Deliteful Dairy also offers educational tours and experiences for visitors of all ages. Guests can take a guided tour of the farm to learn about the daily operations and care of the cows, or participate in hands-on activities such as milking demonstrations and cheese making workshops. Deliteful Dairy is committed to sustainability and environmental stewardship, employing practices that prioritize the health and well-being of their cows, the land, and the community. Visitors can feel good knowing that they are supporting a local, family-owned business that values ethical farming practices and the preservation of the natural landscape. Whether you're looking to enjoy a peaceful afternoon in the countryside, learn more about where your food comes from, or simply savor the delicious taste of fresh dairy products, Deliteful Dairy offers a delightful and memorable experience for all who visit. Come see for yourself why Deliteful Dairy is a beloved gem in the heart of Williamsport, Maryland.
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Western Maryland Rail Trail

The Western Maryland Rail Trail (WMRT) is about 28 miles long and parallels the C&O Canal Towpath for its entire length. A paved, linear trail, it is suited to anyone seeking a pleasant, leisurely outdoor experience - walking, running, biking, and inline skating. The easy grade and paved surface make this trail ideal for families, the elderly, and persons with limited mobility. The WMRT is wheelchair accessible.

Note: the Indigo Tunnel is closed, so between roughly miles 24–27 users are routed onto the C&O Canal Towpath for about two miles. That section is hard-packed dirt rather than paved and can be muddy after rain.

There are several parking and access areas for the rail trail. One at Big Pool, several in Hancock, one at Pearee Station, and one at Little Orleans. Currently at the Pearee and Little Orleans lots there are portable toilets. They will be removed at the beginning of November. Dogs are allowed as long as they are leashed.

Need a bike rental? Check out C&O Bicycle, 9 S Pennsylvania Ave, Hancock, MD 21750. You can also access the C&O Canal from here!

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Linden Hall Farm & Orchard
Linden Hall Farm & Orchard, nestled at 10224 Downsville Pike in Hagerstown, MD, offers a charming rural escape with lush orchards, seasonal picking, and homegrown goodness. Visitors can stroll among apple, peach, and berry trees, enjoy fresh-baked pies and farm-fresh produce, and savor a slice of small-town Maryland hospitality. A family-friendly destination for weekend outings, intimate events, and seasonal harvests, Linden Hall blends agricultural heritage with modern warmth.
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Lewis Orchards
Nestled in the scenic hills of Dickerson, Maryland, Lewis Orchards at 18901 Peach Tree Rd offers a charming, family-friendly destination for seasonal fruit picking and fresh, locally grown goodness. Visitors can explore sprawling orchards, savor sun-ripened peaches, apples, and berries, and enjoy farm-fresh treats and artisanal goods in a welcoming rural setting. A staple for autumn festivals, weekend family outings, and markdowns on seasonal harvests, Lewis Orchards combines rustic charm with community warmth.
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Margraff Trail System (MTB/Natural)

The Margraff mountain biking trail system is located in the Accident area of Savage River State Forest. It is almost 10 miles in length, and provides mountain biking trails of varied difficulty; beginner, intermediate, and advanced. There is also a 2 mile intermediate adaptive mountain biking loop. These trails can also be hiked. There are gravel roads within this system that provide additional biking and hiking miles. The gravel roads are also open to snowmobiles and horseback riding. There are 4 primitive campsites located within the system. The elevation is 2800 feet and visitors enjoy splendid views all year long.

There are no restroom facilities located on site. Dogs are allowed if leashed.

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FireFly Farms Market - Deep Creek
Our awesome goat and cows’ milk cheeses, gourmet items, locally made gifts, and more. Order a cheese platter, book a pairing, shop our wine selection, and enjoy a coffee and panini at our café. All the while, learn about the cheese made in our creamery only a few blocks away!
Harvest House

TURKEY DINNER

Thursday-Saturday October 9th-11th, 2025

4p-10pm or until sold out Cost $15

Dine in and Carry out

Menu:

Turkey Dinner Panini