Portland, Maine, is a hidden gem that offers the perfect blend of vibrant city life and scenic coastal charm. Known for its thriving food scene, Portland boasts award-winning restaurants, fresh seafood, and craft breweries that have earned it a reputation as a culinary haven. The historic Old Port district, with its cobblestone streets and unique shops, provides a glimpse into the city’s maritime heritage while offering plenty of opportunities for shopping and sightseeing. Our Portland Weekend Bike Tour explores the city and islands of our home town.
Check out the tour’s itinerary below and if you have any questions, please get in touch.
Summer Feet guides will meet you in Portland.
June 13-15
September 19-21
October 17-19
Price: $1695 per person
Single Supplement: $600
Guides will meet you at the Portland REgency for a bike fitting. On the short ferry ride to Peaks Island, you can enjoy great views of downtown Portland, Fort Gorgeous, and Casco Bay.
A few small hills will get us onto the road around the island. We will stop at Battery Steele to learn how this small island played a vital role in two wars.
We will cycle the island’s coast for stunning views of the Ram Island Ledge Light,
A late afternoon ferry returns us to the mainland for dinner at a local favorite.
After breakfast at the hotel, we hop on our bikes and pedal the Eastern Promenade Trail out of town and north towards Falmouth. Our route past stately homes leads us to Cousins Island. A short ferry ride takes us to Chebeague Island, the largest island in Casco Bay. We cycle the quiet roads of Chebeague and enjoy lunch before and afternoon very carries us back to Portland
After breakfast, we will pedal across the Casco Bridge and along the country roads of Cape Elizabeth. We will pedal the coastal road back toward Portland, visiting the lighthouses along Casco Bay. The first stop is Two Lights at the tip of Cape Elizabeth. From here we will pedal to the Portland Head Light, first lit in 1791 where we stop for lunch overlooking the ocean. After lunch, we will visit Spring Point Ledge Light and The Portland Breakwater Light, known by locals as Bug Light, before pedaling back into Portland for the end of of our tour.
