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Trip Code: HAR
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From Discovery and CruisingTo Challenging
Nova Scotia’s South Shore and Annapolis Valley offer some of Canada’s most inviting coastal and countryside cycling routes. Following historic railway corridors, this journey moves through charming harbour towns, open valleys, and landscapes shaped by centuries of maritime and Acadian life.
Beginning in Halifax, the route traces sections of the Rum Runners and Harvest Moon Trailway, linking fishing villages, coastal communities, and farmland at a relaxed, engaging pace. Along the way, you’ll encounter UNESCO World Heritage sites, colourful waterfronts, communities known for their warm Maritime character, and local flavours, including Nova Scotia's appellation wine, Tidal Bay.
This supported self-guided adventure allows you to explore at your own rhythm, leaving room for detours, tastings, and meaningful encounters. Whether you’re drawn by ocean views, heritage sites, fresh seafood, or the vineyards of the Annapolis Valley, the journey offers a memorable experience.
Introductory to Moderate
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Day 1
Arrive in Halifax
On arrival, make your way to our centrally-located Halifax accommodation and spend the rest of your day exploring Nova Scotia’s vibrant capital. Stroll to the iconic harbor, the Halifax Citadel, and museums dedicated to rich local maritime heritage. Experience fine seafood restaurants, great shopping, and an optional guided e-bike tour of the city is available upon request. (Tours meet at 9:40 AM or 1:40 PM: tours are based on availability and must be requested 45 days before departure; additional cost applies).
Meals: Nil
Day 2
Transfer to Lunenburg via Peggy’s Cove
Begin the day with a visit to Peggy’s Cove, where smooth granite shores and the iconic Peggy’s Point Lighthouse meet the Atlantic. From here, our driver will bring you to the historic port town of Lunenburg. This UNESCO World Heritage site, founded in 1753, is known for its colourful waterfront and relaxed coastal charm. After settling in, the afternoon is free for you to go and explore museums, galleries, and seaside streets, or venturing out for a bicycle ride to Blue Rocks (12 km / 7.4 mi round trip). Avid road cyclists have the option to take the loop road and ferry to the artsy community of La Have (35km/21.mi), though we recommend extending your stay in Lunenburg if you intend on this.
Meals: B
Day 3
Cycle to Chester (~40km/24.8.mi; +/-40m/130ft)
Along the route today lies one of Canada’s most beautiful communities. Leaving from Lunenburg’s old train station, the Rum Runners trail leads north to Mahone Bay, a waterfront community known for its artistic spirit and easygoing pace. Take a leisurely lunch, browse harbourfront shops, and soak in the atmosphere before continuing past sparkling Oakland Lake and on to Chester. Settle into a cozy inn and enjoy the charm of this welcoming sailing town, with its lively harbour and excellent small restaurants. If time allows, a ferry visit to Big Tancook Island offers a memorable way to end the day.
Day 4
Transfer to Grand Pré, Cycle to Wolfville (~11.4km/7.1mi)
Today, you’ll visit Grand Pré, located on the unceded territory of the Mi’kmaw and one of the most historically significant landscapes in Atlantic Canada. This UNESCO World Heritage site is defined by sweeping marshlands and a remarkable agricultural system developed by the Acadians in the 17th century. Through an intricate network of dykes and aboiteaux, generations carefully adapted the land to withstand tidal ranges of up to 11.6m/5.2 ft, shaping historic farmland that reflects centuries of Acadian life. From here, cycle on to Wolfville, set in the heart of the Annapolis Valley and surrounded by its renowned wine country. Settle into a welcoming B&B for the evening, with time to explore the vibrant town or enjoy tastings at nearby wineries, breweries, or cideries.
Day 5
Explore Wolfville (Up to 56.2km/34.9mi)
This is an ideal day to plan ahead and book a tasting, with many of Wolfville’s wineries and cideries easily reached by bike via the Harvest Moon Trailway. Set within Nova Scotia’s wine country, the Starrs Point Loop offers a rewarding ride, including an optional climb to the Blomidon Look-Off for sweeping valley views. Time in Wolfville lends itself to savouring local fish and chips or visiting the lush botanical gardens.
Day 6
Cycle to Kingston, Transfer to Annapolis Royal (52.3km/32.5mi; +/-82m/262ft)
Enjoy a hearty breakfast and hop on your bike. Today you’ll cover more distance, but you’ll cycle on a mostly flat and straightforward route. Cycling to the meeting point in Kingston brings the reward of a relaxed, pub-style lunch before we pick you up for the drive to Annapolis Royal, a historic port town on Nova Scotia’s northern shore. Time here allows for visits to the Historic Gardens and Fort Anne National Historic site, showcasing a firsthand look into Acadian culture and the region’s early history dating back to the 1600s.
Day 7
Explore Annapolis Royal (~20km/12.4mi to ~53km/32.9mi)
Annapolis Royal offers several cycling options for the day. Option A (~53 km / 32.9 mi) follows Victoria Beach Road on a scenic out-and-back route. Grab a packed lunch from town before you hit the trail. Option B (~20 km / 12.4 mi) includes more elevation and travels along a quiet road to the fishing community of Parker’s Cove. Option C (~53 km / 32.9 mi) passes Cornwallis Park and its beach on the way to Bear River. Whichever route you choose, we recommend you join the optional must-see graveyard tour in Annapolis Royal, lit by lanterns and candlelight, offers a fitting close to your time in the Annapolis Valley.
Day 8
Return to Halifax (drive time ~2.5hrs)
The final morning in Annapolis Royal allows time for breakfast and a leisurely morning before an afternoon transfer back to Halifax. Services conclude on arrival, with additional nights available upon request.
What's included
What's not included
Combination of B&B's and Inns. All have been chosen for their convenient locations, local character, and quality. The trip price is based on 2 people per room. Please indicate if you prefer to share a bed, or have separate beds. A single supplement is available for those wishing to secure their own rooms, subject to availability.
Modern hybrids suitable for road and mild off-road use with eighteen to twenty-four gears. They are provided with helmet, lock, bike bag, and repair kit.
E-bike upgrades are possible upon request, subject to availability. Equipped with helmet, lock, bike bag, stand and repair kit. Great option for a boost and extra pedal-power!
The Rum Runners Trail and Harvest Moon Trailway follow converted railway lines (‘rails to trails’), making them among the flattest cycling routes in the region, with grades under 2%. Note that trail conditions vary by section, as maintenance is shared between communities. Most of the Rum Runners Trail features a crusher dust surface well suited to hybrid bikes and riders of all abilities, though some sections may include loose gravel or uneven patches. Accessing accommodations involves short sections of road riding, which have been kept to a minimum wherever possible. These roads are shared with vehicle traffic, though drivers in Nova Scotia are generally courteous and accustomed to cyclists. Additional road-based loops and out-and-back rides are available, but these routes are hillier and better suited to experienced, road-savvy cyclists. As this is a self-guided trip, participants should be comfortable navigating with maps and route notes, making basic bike adjustments, and handling minor issues such as a flat tire using the included repair kit. Occasional route-finding challenges are part of the experience, and most travellers quickly find their rhythm, often with help from locals along the way. Detailed route materials are provided, along with access to a 7-day service hotline for support if needed.
Per Person, Twin Share
Yes, though you are encouraged to bring your own bike helmet if possible.
Rating: ☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆☆
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Everyone who works with us, from our office staff, ground staff and guides is the ‘’real deal’’. Our team is comprised of actual hikers and cyclists who have explored or live in the region in which you will be travelling. Our entire network is highly-specialised in active travel.
Quality services at the best price make our adventures great value for money. Having essential items included like National Park fees, charming accommodations, most meals, bikes for cycling trips, maps and support for peace of mind. Our inclusions allow you to better budget for your big adventure.
We look beyond the horizon to find new and exciting adventures. We’re passionate about shaping the next generation of outdoor travel in Canada, and constantly seek different ways, routes and alternatives to exceed our clients’ dreams.
We are committed to responsible travel and true sustainability, formed when the company was established, and in the face of a multitude of threats to the environment, our commitment is stronger than ever. We aim to "leave no trace" in both an environmental and cultural sense.
6Days
Moderate
Introductory
7Days
8Days