Step Out of the Ordinary
There is no season quite like fall in Nova Scotia. Across Cape Breton, the foliage comes alive in fiery shades of red, orange, and gold. It’s an invitation to get outside and experience an unforgettable coastal journey.
Discover the perfect blend of culture, cuisine, and natural wonder that makes Cape Breton one of Canada's most memorable destinations.
This fall, step out of the ordinary with a stay at The Simon Hotel Sydney, where stylish comfort meets warm maritime hospitality right in the heart of downtown. Book a stay between August 27 to October 31, 2026 and receive two great perks:
- A box of bite-sized fudge from local Cape Breton Fudge Co.
- $20 in Sydney Downtown Dollars to spend at participating downtown businesses
Embark on the Ultimate Nova Scotia Fall Journey
There’s more to a trip to Nova Scotia than the destination. Make it a journey of unexpected discoveries, colourful landscapes, and crisp autumn air.
Extend your stay in Sydney with a scenic drive toward our sister property, Oak Island Resort & Conference Centre in Western Shore. Give yourself permission to wander and swap the highway routine for breathtaking vistas and local hidden gems.
Here are some of our favourite stops along the way.
Kidston Lighthouse, a short ferry ride from Baddeck
The beautiful views across Bras d'Or Lake give the lighthouse the reputation of being one of Cape Breton's most picturesque waterfront views. The perfect location to take a breath and just be present.
Egypt Falls near Margaree Harbour
Hike to one of Nova Scotia's most spectacular waterfalls. Hidden within the forests of Cape Breton, your efforts will be rewarded when you reach the cascading water of one of Cape Breton's best-kept natural secrets. Snap some pics to capture the moment.
Dancing Goat Cafe & Bakery in Margaree Valley
Why this bakery? It’s an icon! Nestled in the scenic Margaree Valley along the world-famous Cabot Trail, it’s a well-loved gathering place for both locals and visitors. The fresh-from-scratch baking, artisan breads, specialty coffees, and hearty breakfasts and lunches, offer an authentic taste of Cape Breton hospitality.
Charlene's Family Restaurant in Whycocomagh
Overlooking the Bras d'Or Lake region, Charlene’s is a must-visit destination for authentic Cape Breton comfort food. Award-winning seafood chowder and homemade pies from family recipes create an unforgettable treat for your palette.
Tourism Nova Scotia / Photographer: Acorn Art & Photography
Masstown Market
This is no mundane rest stop. It’s practically a rite of passage! This village-style complex focuses on local Nova Scotia products, from the bakery to a deli to fresh local seafood, you will also find a gift shop, liquor store, and gardening and floral shop. It goes way beyond your regular highway stop.
Tourism Nova Scotia / Photographer: Jake Brenner (@jakesescapes)
Chester
Peaceful and unassuming, this idyllic coastal town has a pedestrian-friendly village with charming indie boutiques, art galleries, craft shops. The picture-perfect architecture of the historic homes is inspired by New England. The town is best known for being a world-class yachting hub and home to one of the most stunning 18-hole golf courses in Atlantic Canada.
Discover Oak Island
We hope you’re inspired by the amazing locales and vistas of this off-the-beaten-path journey. Only 15 minutes from Chester, make your way to Oak Island Resort & Conference Centre as your last stop.
Teaming up with The Simon Hotel, this beautiful, oceanside resort is the perfect place to rest and reflect on your travels across western Nova Scotia.
Make the journey part of the getaway
The best fall trips aren’t always about getting there quickly.
They’re about discovering a new roadside view. Finding a bakery you didn’t know existed. Taking the scenic route. And remembering that sometimes, the detours are the destination.
Terms & Conditions
*Subject to availability at time of booking. Must book by October 28, 2026. Valid for stays between September 13 to November 19, 2026. Rate quoted is per room, per night, based on double occupancy. Taxes are extra. For new bookings only. Blackout dates include but may not be limited to October 11, 2026. May not be used in conjunction with any other specials or offers. Not applicable to groups.