- Difficulty: Moderate (distance dependent, slight grades).
- Facilities: Parking, Visitor’s Center, exercise station, parks, playground, food & drink, all directly accessible from the trail.
- Signage: Information kiosks with large maps & signage at key points.
- Categories: #Accessible, #Bridge, #Camping, #Lake, #Playground, #Rails-To-Trails, #River, #Snowshoeing, #Swimming, #Wetlands.
- Features: 35km of compacted crusher dust rails-to-trails. Scenic crossings, including 15 bridges. Art installations. Direct access to 2 hiking areas. Nearby Graves Island Provincial Park campground. Part of the Rum Runners Trail (123 km from Halifax to Lunenburg).
The Chester Connection Trail
The Chester Connection Trail links to the Dynamite Trail in Martins River and the Aspotogan Trail in East River. It forms part of the larger Rum Runners Trail, which stretches from Halifax to Lunenburg. Nestled along Nova Scotia’s scenic South Shore, the Chester Connection Trail stretches a peaceful 35 km from Martins River to East River in the Municipality of Chester. The Municipality officially opened the 35-kilometre Chester Connection Trail in 2003, with the Rum Runners Trail officially opening in 2017. You can use the Chester Connection as a gateway to longer adventures toward Halifax or Lunenburg.
The Rum Runners trail gets its name from the South Shore transportation route for the lucrative Rum Running operations, which coincided with Prohibition in the United States (1920–1933) and Nova Scotia’s own temperance laws, which began in 1910 and expanded in 1921. The hundreds of offshore islands and hidden coves along the South Shore were ideal for boats to stealthily unload and transport their cargo along the railroad.
Built on a decommissioned railway corridor, this compacted crusher dust, rails-to-trails path now invites walkers, cyclists, and wanderers to explore its gentle terrain and calm surroundings. The multi-use trail is for walking, cycling, horseback riding, and off-highway vehicles. The flat terrain of the former railbed makes it suitable for users of all ages and abilities. The trail is open year-round, with winter activities such as snowshoeing, fat biking, and off-highway vehicles permitted.
In addition to being ideal for biking, the trail is great for other activities. Walking: enjoy peaceful strolls or brisk walks through forested areas and scenic bridges. Picnicking: Pack a lunch and enjoy a meal at one of the trail’s rest areas. Geocaching: Join the global treasure hunt with caches hidden along the trail. From start to finish, the Chester Connection isn’t just a trail—it’s a journey through flavours, landscapes, and the laid-back rhythm of coastal life.
Famous to treasure hunters, folklore & history buffs worldwide for being home to Oak Island, the true treasures in this area can be found with a ride on the Chester Connection Trail. The Trail exemplifies how disused rail corridors can be transformed into vibrant community assets, blending recreation, heritage, and sustainability.
Trail Rules
You are responsible for your own safety while on the trail; therefore, exercise caution at all times. Keep in mind the following rules while using the trail:
- Motorcycles, automobiles, trucks, sport utility vehicles that are registered for the road are not permitted at any time.
- Off-Highway Vehicles, including dirt bikes, that are registered as Off-Highway Vehicles, are permitted.
- Maximum speed is 20km/hr by any mode of transport
- No person shall use the trail between 11:00 pm and 6:00 am of the following day.
- All pets must be on a leash.
- No hunting or trapping is permitted.
- No person shall have in their possession or discharge a loaded firearm or bow.
- No person shall have in their possession an unloaded firearm or bow unless permitted under the Wildlife Act.
Please follow basic Leave No Trace outdoor ethics on all of your wilderness adventures. Always pack basic safety & survival equipment.
Trail Maps & Parking Areas
There are 3 main parking areas along the trail, and a couple of other smaller access points. From North to South, they include: a large parking lot in East River at the Northernmost part of the trail, where it meets the Aspotogan Trail. A large parking area at the Chester Visitor Information Centre is located near the midpoint of the trail in the town of Chester. A small pull-off area on Highway 12, next to a church in Chester Basin, and a small parking area in Martins River near the southernmost part of the trail, where it meets the Dynamite Trail.
Large trail maps are posted at the information kiosks located near the East River, Chester Visitor Centre, and Martins River parking areas. The maps show both the local section of the trail as well as the whole Rum Runners Trail, which in turn is part of a 3000km network of cycling routes around the province called the Blue Route.
Use my custom Google Map of the Chester Connection Trail and the entirety of the Rum Runners Trail, linked near the top section of this guide. You can use it to navigate on the go, as laid out in my basic how-to guide.
Exploring The Trail
Starting from the Northernmost section, you’ll immediately cross one of the most scenic parts of the trail, the East River Bridge, one of 15 bridges on the trail and one of 12 old railway bridges in the municipality of Chester. 1.5km from the East River Bridge, you’ll come to a great stopping point on peaceful Labrador Lake. At the far end of the lake, you’ll come to the trailhead for Castle Rock Hiking Trails. The spectacular view atop “Castle Rock” is well worth the hike.
4km from the Castle Rock trailhead, you’ll come to a picnic table at Goat Lake, which is another quiet & peaceful place to stop. Just under 3km from Goat Lake, in East Chester, you can exit the trail and take a short jaunt on the main roads to reach Graves Island Road, and beautiful Graves Island Provincial Park, with picturesque oceanside campsites.
Another 4km on from Graves Island, you’ll reach the Chester Visitor Center, a former full-service train station, built in 1905. Now run by the Chester Municipal Heritage Society, you’ll find a gift shop featuring local artisans and seasonal goodies, and the Visitor Information Center, featuring train station antiques and a Discover Oak Island display.
4.5km away from the Visitor Center is the trailhead for the recently opened Haughn Natural Area. This 28-acre site has 3 different trails to explore, ranging from 1200m to 200m. After passing over a few small bridges, 4km from the Haughn Natural Area, you’ll come to the trail access & small parking area off of Highway 12. Directly on the trail is a fitness park. A small playground & basketball court are located a few meters away on Croft Road.
2km from Croft Road, you’ll come to the Gold River Bridge and a subsequent detour. The Gold River Bridge is the longest and highest span at 367 feet long and 56 feet high. Unfortunately, it has been closed since 2021 due to extensive damage from flash flooding. There is no estimated finish date for repairs. You’ll have to detour here onto main roads and a small section of highway that crosses the Gold River. This is a good opportunity to stop in the Gold Bean Cafe or the adjacent convenience store before getting back on the trail, which is located directly behind the Cafe.
Just over 5km from the Gold River Bridge detour, after crossing a couple more small bridges, is Trail Burger, a summertime seasonal, trail-side hidden gem that serves up satisfying takeout without requiring you to leave your path. 2km from Trail Burger, you’ll come to the final stop, the Martins River parking area. 1km from this parking area is the scenic Martins River Bridge & the beginning of the Dynamite Trail leading to the picturesque village of Mahone Bay.
Biking Adventure
The surface of the trail is crusher dust and this, combined with the flat terrain, makes it ideal for easy travel. This is a multi-use trail, so you should expect to see walkers, cyclists, off-highway vehicles and even horseback riders. In the winter, you may come across people on snowmobiles, skiing and snowshoeing. This multi-use nature can also contribute to occasional piles of loose gravel & potholes, especially during the Spring thaw. Gravel bikes, hybrids & cruisers can tackle this trail with ease.
Make sure to pack sunglasses if you’re biking early or late in the day, as the sun can be directly in your face for some stretches. Helmets are a must. Lights and a bicycle bell are highly recommended for visibility and safety. It’s common courtesy on multi-use trails to announce your presence with the “ding” of a bell when you’re passing others. Keep in mind that all trail users must yield to horses, and the maximum speed limit for all is 20km/h. Don’t leave anything of value in your car, and hide all items from view to avoid being an inviting target for thieves (advice for all trail parking, no matter where).
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Trails like this thaw slowly, making them wet, soft & susceptible to damage in Spring. Combined with blackflies and mosquitoes coming out, Spring is a season where you’ll have to take these conditions into account when deciding if you’re equipped for the conditions. Summer and Fall are often ideal conditions. Warm winter stretches can make for wet conditions similar to early spring, but after snowfalls, the trail is only conducive to fatbikes. The earlier after a snowfall, the better, as ATV tracks get laid down quickly in many sections. Keep in mind that the parking lots may not be plowed if it is soon after a snowfall. Autumn brings vibrant colours that create a kaleidoscope-like atmosphere, making it very photogenic.
Many of the stops along the trail, such as Castle Rock hiking trail, Haughn Trails & Chester Visitor Center, have bicycle racks to securely lock your bike. If you plan on stopping at any of these places, make sure you bring a good lock. A rearview mirror is useful to keep an eye out for ATVs & other bikers. Fenders are good for wet conditions to keep mud & puddles from ruining the vibe. Eliminate phone anxiety by bringing an external battery to keep it topped up, no matter how long your outing turns out to be.
The southern sections of the trail have frequent yields and stops where the trail intersects with private driveways and roads. You’ll have to keep your eyes and ears peeled for cars, and head on a swivel in order to obey all stop and yield signs and avoid an accident.
The Northern sections wind through some remote areas, so be sure to prioritize safety and preparedness. Especially if you plan on doing some hiking on the side trails, pack all survival essentials, including water, first aid, an emergency blanket, and a compass. Cell phone coverage can be spotty, so be sure to tell someone your plans and what time you expect to be done. These quiet stretches are great for wildlife watching, offering opportunities to spot birds, deer, and other local fauna. You can view the most commonly observed species on iNaturalist.
Chester Connection Trip Tips
45 minutes from downtown Halifax, the Chester Connection Trail can be easily done as a day-trip from the city. Unfortunately, there aren’t any public transportation options, but Maritime Bus runs routes from Halifax to Exit 9 in Chester. For those with electric vehicles, EV charging on the South Shore is currently sparse, but the Gold Bean Cafe and adjacent Gold Nugget convenience store, run by Wasoqopa’q First Nation, offers 2 free J1772 chargers for customers, making it a perfect stop for EV owners. Oak Island Resort offers a free J1772 charger for its guests. Fortunately, 180kw fast chargers will soon be opening in Chester Basin to eliminate range anxiety for this portion of Nova Scotia’s South Shore.
The closest bicycle rentals are Hubbards Cove Rentals, nearer the Aspotogan Trail, and Sweet Ride Cycling, nearer the Dynamite Trail in Mahone Bay. The latter offers e-bikes.
If you intend to visit during Chester Race Week in August, anticipate unusual amounts of traffic, busier than usual shops & accommodations that require booking far in advance. Race week is the largest regatta in Eastern Canada, making the town a bustling hub of activity during this time.
There’s plenty to explore throughout the trail; no matter what sections you do, there are always points of interest and places to stop. On-trail points of interest include art installations featuring work by local artists. There are currently 7 installations found along Chester Municipality’s trails. They make for good stops to take a breather and be present. Most are interactive pieces, inviting you to participate. Visit all 7 over the course of one year to collect the Chester Art Adventures Badge as part of Hike NS’s Hiker Challenge.
Side Quests
There are two hiking trails accessible directly from the Chester Connection Trail. Castle Rock Trails are a 3km return-trip hike with a spectacular view. South of Chester, Haughn Estate and Natural Area offers 3 peaceful, accessible woodland trails.
Off Frank Swinimar Road is the picturesque Gold River-Western Shore waterfront walkway with views of Oak Island. This 500m walkway is bounded to the north by The Island View Restaurant, offering fresh seafood, ice cream & other satisfying treats.
Chester Attractions
Explore trail-to-table experiences in the charming seaside town of Chester. Quaint streets lined with boutique shops offering handcrafted goods, cozy cafés serving up fresh pastries and locally roasted coffee, and art galleries showcasing the work of talented regional artists. The vibrant Chester Art Center hosts rotating exhibitions, workshops, and community events.
In summer, cool off at the Lido pool. This saltwater swimming spot is right on the ocean’s edge. Its ocean views and relaxed atmosphere make it a perfect place to take a dip or lounge in the sun. An on-site public washroom makes for an easy wardrobe change. It even offers free public wifi to get caught up or check in.
The Chester Visitor’s Information Center is more than just a place to grab a map; it’s a gateway to the town’s heritage and community spirit. This former rail station now features a railway museum complete with vintage artifacts and stories from the golden age of rail. Browse the separate gift shop for souvenirs and locally made goods.
The adjacent Farmers’ & Artisan Market is a lively outdoor gathering which operates every Friday morning, from May to October. You’ll find fresh produce, homemade treats, handcrafted jewelry, and unique gifts, all sourced from local makers and growers.
The Town of Chester has a rich culture of environmentally sustainable living, which you’ll see reflected in your explorations. Check out the Friends of Nature Society, one of North America’s oldest conservation societies, based in Chester, to learn about and support the causes currently on their radar.
Accomodations
Graves Island Provincial Park campground is open from mid-May until mid-October. Offering 50 unserviced, 33 serviced, and 12 walk-in campsites. One of the province’s most popular Provincial Park campgrounds, you’ll want to book well in advance to ensure your spot.
Near the town of Chester, you’ll find several Inns, B&B’s and cabins. Click here for a Google Map listing of ones nearby. Other quaint stops & stays, such as River Ridge Lodge, are located at the southernmost point of the Trail, where the Chester Connection meets the Dynamite Trail. World-famous Oak Island is home to a beautiful 4-season resort & conference center located near the southernmost section of the Chester Connection Trail.
Tips on places to check out near the trail? Leave your recommendations in the comments below.
A bike ride on #NovaScotia's Rum Runners Trail to the trailhead of Castle Rock hiking trail:
