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MV Bike Tour #14: Up-Island!

Language: English
31 Stops 68.7 miles · Bicycle · Adult, Teen
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  • The iconic Gay Head cliffs & Gay Head lighthouse
  • Quintessential New England country lanes & picturesque hamlets
  • Bucolic, stonewalled New England farms, nature preserves & sandy, rocky beaches


This is a long (~40 mile plus round trip), challenging, up-island tour intended for advanced riders! There are NO bike paths up-island, and as this is for advanced riders, the routes from down-island to get up-island may not have bike paths either. The up-island roads are generally curvy and hilly, with 35 mph plus speed limits and narrow edges. And it's not called "UP-island" for nothing!! Well, actually, it probably got that name because it was usually UP wind, along Vineyard Sound from Holmes' Hole (Vineyard Haven), in the days of wooden ships and iron men. However, on most of the tour's route, traffic is usually light and most Vineyard drivers will give bicyclists the right-of-way and drive carefully around them, but caution is still strongly advised: PLEASE RIDE SINGLE FILE AND WITH TRAFFIC!! If you're not confident, experienced or ready to do this, drive your car up-island instead! And watch out for bicyclists! Recent changes to the Massachusetts motor vehicle laws now mandate that motorists must give cyclists at least 4 feet of clearance when passing - even if the auto must go into the on-coming traffic lane. And please remember that bicycles, as vehicles, have the right to use an entire lane of the road - regardless of whether there is a bike path available. Starting in either Vineyard Haven, Oak Bluffs or Edgartown, the tour goes on many of the less-traveled, most beautiful, sun-dappled, quintessentially New England country lanes on the island, and passes many small, bucolic, stone-walled, New England farms, quiet, wooded nature preserves, and magnificent sandy and rocky beaches. It goes through the small (don't blink!), picturesque wide-spots-in-the-road of West Tisbury, Chilmark, Aquinnah and Menemsha, and explores the iconic Gay Head Cliffs and historic Gay Head Lighthouse. To get back, the tour retraces itself back to the initial routes from each town. But first, you gotta get outta town!! From Oak Bluffs follow Stops 1-6, to the first up-island Stop 8. From Vineyard Haven, follow Stops 9-13, to Stop 8. From Edgartown, start at Stop 7, to Stop 8. Or from wherever you are, let the App direct you to Stop 8, by choosing Stop 8 and following the route provided by the App. Then follow the tour from there. And after all that riding, you gotta pedal back! But wait - there's an alternative! Take the bus! All VTA busses have a 3-bike rack on their front and will be happy, for a small exact fare, to take you and your bike, with possible transfers, to any place on their multiple routes. There are a variety of day, month or year VTA passes available, too! The website is: https://www.vineyardtransit.com for routes and schedules. But if you feel you MUST pedal back, go to stop 30, and turn left onto Old County Rd for VH (Stops 13-9); or continue straight on the ET-WT Rd, to turn left on Barnes Rd, at stop 31, (Smokey Bear) for OB (Stops 5-1); or just continue straight on ('till morning ...) on the ET-WT Rd for ET (Stop 7). Have a great ride!! Difficulty: Advanced! Bike Paths: Up-Island (after stop 8): NONE; Down-Island: ~50% Maximum Elevation Gain (from VH): 590 ft Maximum Elevation Loss (from VH): 489 ft
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Route Details

Oak Bluffs start (SSA ferry terminal)

0.2 miles

Circuit Ave, Oak Bluffs

1.3 miles

Oak Bluffs Fire Station

1.96 miles

28 more tour stops

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