Self Guided Walking Holidays & Cycling Holidays

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Explore old-town Lunenburg, a UNESCO preserved colonial settlement


  • Explore the iconic community of Peggy’s Cove and its famed lighthouse
  • Bike from village to village as you follow the Rum Runners Trail along Nova Scotia’s southern coastline
  • Feast on lobster suppers, pan-seared scallops and smoked haddock fresh off the boat
  • Discover Oak Island, from the History Channel’s hit series “The Curse of Oak Island”
  • Explore old-town Lunenburg, a UNESCO preserved colonial settlement

Explore the beauty, charm and history of Nova Scotia’s South Shore on bike paths, cruising through wooded forests to overnight seaside villages.

Begin your adventure with an exclusive tour of Peggy’s Cove, an iconic and picturesque fishing village in Nova Scotia. Pick-up your bicycle and pedal along the “Rum Runners Trail,” a bike path drawing its name from the region's prohibition-era history and connecting the attractive coastal villages along Nova Scotia's South Shore. Cruise from Hubbards all the way to Lunenburg, enjoying lobster suppers, historical landmarks and optional seafaring activities along the way. Bike to Blue Rocks and wander the narrow streets of Lunenburg, a UNESCO heritage site and one of the best preserved Colonial settlements in North America.

Each night, stay in charming B&Bs along the route and within walking distance of harbors, shops and top seafood restaurants for a classic maritime adventure.

Day 1: Arrive Halifax

Downtown Halifax can be easily reached by taxi upon arrival from the airport (approx. $65 CAD, 30 min).

Check in to your hotel and head to the waterfront boardwalk, passing unique shops, bustling restaurants and graceful tall ships. Enjoy a stroll through the Public Gardens, explore the oldest farmers market in North America or visit the Titanic and Maritime Museum for captivating memorabilia. Halifax boasts more pubs per capita than any city in Canada, so make sure to stop for a cold brew and ale-battered fish and chips, a local favorite.

Overnight: Halifax

Day 2: Discover Peggy’s Cove & Bike to Hubbards

This morning, meet your driver for a private tour of Peggy’s Cove, one of Nova Scotia's most iconic sites. Explore this preserved fishing village famed for its lighthouse, traditional homes and white-washed boulders facing the Atlantic Ocean.
Continue the tour to the Bike & Bean Café and Bike Shop to grab lunch and pick up your bike for the start of your cycling adventure! The shop is conveniently located on the Rum Runners Trail, so enjoy your first day’s pedal to the seaside village of Hubbards, and your overnight stay. Tonight, head to the Shore Club, a local hot spot, famous for its fresh-caught lobster suppers, all-you-can-eat salad bar and festive  venue hosting dancing with live bands.

Tour: Highlights of Halifax & Peggy’s Cove (included, approx. 4 hours)

Bike: 15 mi. (+78/-171ft.)

Overnight: Hubbards

Day 3: Bike to Chester & Afternoon Adventure

Enjoy a flat, easy morning ride through wooded forest to the next village located on the Chester Peninsula.

In Chester, drop off your bikes at your B&B or ride into town to roam the streets, savor a lobster roll, visit an art gallery or browse local souvenir and antique shops. Take the rest of the afternoon to enjoy the numerous seafaring and outdoor activities, all within walking and biking distance from town. Cycle over to the Chester Golf Club to enjoy an 18-hole golf course. Bring your bike to the wharf to catch a ferry to Big Tancook Island for a unique island cycle (measuring 2.5 miles around). Head to the harbor to join a Chester boat tour or to rent a sea kayak or paddle board and explore the peninsula’s coastline for an afternoon of open water adventure (not included).

Bike: 17.5 mi. (+249/-167ft.)  

Overnight: Chester

Day 4: Bike to Lunenburg & Discover Oak Island

This morning, continue pedaling along the Rum Runners Trail through open forest and rural communities. Upon reaching the town of Western Shore, veer off the trail to cycle the paved road leading you to the Oak Island Interpretive Center, open to the public. View displays and exhibits describing the history and mysteries of one of the world’s largest treasure hunts. For Oak Island fans, join the 10:00 AM boat tour departing the Oak Island Resort for
extra exposure to the hit TV series “Curse of Oak Island," (approx. 1.5
hours, $60 CAD per person, not included).

Continue onward to Mahone Bay, a stunning coastal town perfect for lunch and homemade ice cream. Pedal the last section into Lunenburg, a UNESCO historical site and original home to the famous Bluenose schooner, a fishing vessel and  international racing ship that went undefeated for 17 years.

Bike: 26.5 mi. (+259/-340ft.)

Overnight: Lunenburg

Day 5: Bike to Blue Rocks & Explore Lunenburg

Enjoy a short bike ride along back country roads to the tranquil bay of Blue Rocks (4.5 miles each way). This lonely, quaint town is a hidden gem, popular with photographers, artists and sea kayakers who delight in its scenic shores and views of the bay. Stop by The Point General, one of three buildings in town, for coffee, tea, fresh baked pastries and hand-made goods.

Rent a kayak or join a guide for an incredible paddle around the bay and nearby islands (not included). Pedal back to Lunenburg to spend the rest of the day discovering this well-preserved historic settlement. Join a walking tour, or a ghost tour or pick-up a map to visit churches, houses, the rum distillery and famous landmarks encompassing Lunenburg's rich heritage. Walk along the waterfront or board the Eastern Star Sailboat (available June-October) for a sunset sail and spectacular panorama of Lunenburg's colorful port (not included).

Bike: 9 mi. (+46/-105ft.)

Overnight: Lunenburg

Day 6: Onward Travel

Depending on your travel arrangements, enjoy a hearty breakfast and morning stroll before transferring back to Halifax Stanfield International Airport or downtown Halifax (included).


We specifically hand-pick your accommodations in comfortable and
charming B&Bs to ensure that you enjoy every minute of your stay
while exploring Nova Scotia. 

All accommodations are located along the bike route and offer a warm
welcome to tourists and cyclists. Additionally, each offers individual
character and welcoming hospitality.

Single Rooms & Solo Travelers

This trip is based on two people sharing a room. If you’d like separate rooms, a single supplement is required.

If you would like to request a twin room (same room with two separate
beds), please notify us during booking so we can request this option.

Due to the amount of tourists traveling the area and frequenting the
Rum Runners Trail, this trip is also available to solo cyclists (a solo
supplement is required).


Breakfast is included each morning and ranges from buffet style, a
breakfast basket or a set menu. Most breakfasts include a hot dish
(eggs, pancakes or waffles), coffee, tea, yogurt, granola, fruit and
baked goods. Due to the small fishing village charm, proximity to the
sea and distance from Halifax, all B&Bs pride themselves on serving
fresh and seasonal cuisine straight from the ocean, garden or local
farmers market.

Lunches and dinners are not included in this trip, so you can choose
from nearby options. For lunches, you can find cafés or restaurants
located in towns along the biking route. For dinner, you can dine at
local restaurants all within a short walking distance from your night’s
stay. Due to each town’s location on the coast, we recommend trying out
the amazing seafood restaurants that scatter the towns, delighting on
local delicacies such as lobster, crab, oysters, scallops, Haddock and
seafood chowders.

Extra Nights

You can easily request to add extra nights during this itinerary. For further details, please ask us at the time of booking.



Waverly Inn

Welcome to the Waverley Inn, located in downtown Halifax and walking distance from major attractions, restaurants and the waterfront. Enjoy the relaxed, casual and friendly Victorian style atmosphere, where hospitality is considered a home away from home.







Anchorage House

Open year-round, the Anchorage House is a wonderful winter destination and relaxing summer getaway. Superbly located overlooking the beautiful Hubbards Cove in St. Margaret’s Bay, enjoy relaxing under the stars, taking a beach stroll or exploring the nearby trails.







Mecklenburgh Inn

The Mecklenburgh Inn is an historic turn-of -the-century inn (circa 1902) in the heart of the charming village of Chester. Enjoy the warm welcome of the beautifully furnished rooms, gourmet breakfast, cocktails by the fire and a peaceful slumber.







Boscawen Inn

Overlooking Lunenburg Harbor and the Old Town below, the Boscawen Inn is a special place to stay. As an architectural landmark named for Admiral Edward Boscawen, you can’t miss this lovely Queen Ann style mansion on the hillside.


This trip is available to start on any day of the week from May to October. However, we recommend avoiding a Sunday or Monday trip start, as some recommended restaurants and vendors are closed early in the week.

We suggest you book as soon as your plans are finalized to ensure availability for specific dates. 

When To Go?

The best time to visit Nova Scotia’s South Shore is May through October. Summer and fall provides perfect weather for outdoor and seafaring activities.

If you are looking to avoid the crowds, we recommend visiting in September and October. March and April is also less crowded, yet the early springtime can often bring in rain showers and misty weather. 


Navigating is easy using the Macs Adventure Navigation App. Your daily rides will be mapped in the app with GPX tracks, route notes and turn-by-turn directions. All of these resources are available to download for offline use, which is recommended as cell service along the Rum Runners Trail can at times be spotty.

You will be provided with local bike shop information in addition to 24/7 telephone support for Macs Adventure should you require assistance.

Experience, Fitness & Grade

This tour is graded easy, with four days of biking and a maximum distance of 26 miles. Daily rides average around 16-22 miles (2-4 hours) along wide multi-use gravel paths. The distances and ascents/descents are approximations of the recommended routes.

The route follows the Rum Runners Trail for the entire itinerary except the last day’s ride when biking from Lunenburg to Blue Rocks. When biking to Blue Rocks, bicyclists should expect to ride on two-lane, paved back country roads with minimal traffic.

As a shared use trail, travelers are expected to see pedestrians, cyclists, horses and on the rare occasion, ATVs. Bicyclists should also be prepared for riding on gravel, loose rock, dirt and on rainy days, mud.


Our pre-departure information pack has detailed advice and a packing list on what to bring. This includes warm and cold weather gear, biking gear, rain gear and lots of other specifics.

Please be prepared by packing all the necessary items for a comfortable trip. If you have any questions about what to take, we'd be happy to share our own top tips and advice.  

Bike Rental

Bike rental is included in the cost of this trip. Bike rental includes a Premium Hybrid Bike (Orpheo), outfitted with a helmet, lock and repair kit. If desired, a touring cycle cross bike, electric bike or even a kids tag-a-long bike can be available at an additional charge. We recommend using the flat pedals included with the premium hybrid rental or bringing your own, but avoiding clipless pedals most commonly used for road bikes and paved surfaces.

Please supply us with your height and frame size you currently ride during booking.

Travel Insurance

Travel insurance helps protect your travel investment, your belongings and most importantly you, from unforeseen circumstances that may arise before or during your trip. For more information, please visit our travel insurance page by clicking this link.

Getting to Downtown Halifax

By Air

Halifax Stanfield International Airport, located about thirty minutes from downtown Halifax, has flights from international and national destinations.

By Private Taxi

To avoid the hassle of driving in traffic, multiple bus stops and ease of flexibility upon arrival, we recommend grabbing one of the many taxis lined up outside the arrivals exit (approx. $65 CAD, one-way). If desired, you can reserve a taxi in advance and at a set time with Halifax Airport Taxi (approx. $63 CAD, one-way).

If you would like us to reserve a taxi for you in advance, please notify us during booking (additional costs apply).

Getting from Lunenburg

Included in this trip is a private transfer from your overnight accommodation in Lunenburg back to Halifax Stanfield International Airport (approx. 1.5 hrs) or wherever desired in downtown Halifax (please notify us of this specific location during booking).

Getting Around

For additional transportation services outside the provided itinerary, such as a taxi to a specific restaurant or location, the host at your evening’s accommodation can help assist you in making the necessary arrangements.


  • 5 Nights at hand-select charming B&Bs
  • 5 Breakfasts
  • Private narrated tour of Halifax & Peggy’s Cove
  • Bike rental, fitting and orientation
  • Daily door-to-door luggage transfers
  • Transfer back to Halifax Stanfield International Airport (onward travel)
  • All taxes and fees
  • Macs Adventure Navigation App
  • Route notes
  • Detailed pre-departure information pack
  • 24/7 US telephone support


  • International flights
  • Taxi from Halifax Stanfield International Airport to downtown Halifax
  • All other afternoon activities
  • Lunches, dinners, drinks and snacks
  • Additional nights before, during or after the trip
  • Personal equipment
  • Travel Insurance
  • Gratuities and tips


  • Extra Nights in Halifax, Hubbards, Chester and Lunenburg
  • Single Room Supplement
  • Solo Supplement
  • Room Upgrades (only where applicable)

What is the Rum Runners Trail?

The trail's name originates from the term rum-running, an organized smuggling of rum and other liquor during the Prohibition period between the United States and Canada.

The Rum Runners Trail is a partnership of seven trails linked together to form a continuous trail from Halifax to Lunenburg. Six organizations and appointed town members manage all seven sections of this shared multi-use trail, resulting in a well-maintained trail system for the economic, social and health benefits of local communities.

What if I want to book an optional activity?

One of the perks of this region is that there is a lot to see and do within each overnight town and village along the way. Optional activities include, but are not limited to: Sailing, sea kayaking, island boat tours, walking tours and golf. The Highlights of Halifax and Peggy's Cove Narrated Tour is included in this itinerary, all other activities are optional and at an additional cost. Most activities can be reserved that same day, or the day before. These activities will be outlined within your pre-departure pack, including contact numbers and approximate costs, should you desire to make reservations and payments prior to your departure.

How do I get my rental bike?

Your rental bike will be arranged through a local bike shop at the starting point of the Rum Runners Trail. We will set this up ahead of time and provide all necessary details, including where to leave your bike at the end of the trip, in your pre-departure information packet.

How does the luggage transfers work?

We have arranged for your luggage to be transferred from your accommodation (as per your itinerary) and moved to your next overnight accommodation. Luggage will be picked up from the front desk or reception area around 10:00am of each day and dropped off at that evenings accommodation by 5:00pm. For overnights within the same accommodation, enjoy keeping your luggage with you within your room. We ask you to limit your luggage as much as possible and with a maximum weight of 50 pounds per person.

What if I become ill or can't bike a stage?

If you are not up for biking the entire route, you can stop at any town along the way, or completely avoid the entire route, by transferring to the next town or overnight accommodation. Due to being a high tourist destination, local taxis and car services are available to call. If you are in need of local taxi, we will be more than happy to help. Specifics and contact numbers can be found in your pre-departure information packet, or you can ask the host at your overnight B&B.

If you need medical services, you'll find information in your pre-departure information packet or you can ask for assistance at your B&B. As always, 24/7 support from Macs Adventure is only a phone call away.

Nice, relaxing trip!


Trip worth doing , good variety, do the sea kayak on the last day!




Great family bike tour


This was our third self guided Mac's Adventure self guided bike tour and we enjoyed it greatly and will certainly be looking for more trips like this in the future. This trip is mostly along well maintained rail-to-trail railroad beds, which makes the biking easy, fast, relaxing, and most importantly for us, family friendly. We enjoyed being able to bike along and have relaxing conversations while watching the scenery roll by - rather than hugging the side of a road getting buzzed by traffic. The accommodations were all very comfortable and friendly. Logistically, there were no issues. Taxi and luggage transfers all occurred on time. As far as suggestions/constructive feedback just a couple things: 1) In Chester, the B&B was actually a couple miles outside of the village center, and not near restaurants. My only suggestion here would be to highlight this arrangement in the tour info so there are no surprises, and perhaps offer a downtown alternative when booking as that may be preferable to some. That being said, the B&B was exceptional and worth the added miles (or taxi fare). 2) When approaching Lunenburg, the app's GPS track shows a bee-line to the Boscawen Inn through the busy city center and the tour description warns the final bit is not bike friendly. We discovered an alternate route to the Inn that sticks to rail-to-trail bike paths with a short bit through a quiet residential neighborhood (see image attached) that is very bike friendly.

Smith Family

Freeport, Maine

Nova Scotia: Biking the South Shore

5.0 2


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