Nantucket Island has always been high on my travel list, but for some reason I had never made the trip. Well, thanks to my girlfriend who has grown up visiting I can now check it off my list. Fall is her favorite time to visit because the summer crowds have cleared out which means no long lines, the trees are super colorful and it doesn’t hurt that hotels are much cheaper.
Sticking with our theme of being active wherever we go we took our bikes ($14/rt ea) and left the car in Hyannis ($12/day parking). The ferry ride takes one hour so grab a beer and find a seat on the top deck where you can take in the scenery.
As you’re arriving you will pass Brant Point which has a neat little lighthouse on a sandy point. Great spot to take a few drinks and watch the sunset. From the ferry to our hotel I could already tell was going to love it. Tons of cobblestones, beautiful cedar shake homes with perfectly manicured grounds, and stylish looking bars & restaurants. We checked in to The Veranda House (and grabbed a freshly baked cookie and glass of wine, which they do every night from 4-6 pm), dropped our stuff and headed out to explore for a few hours before having an amazing dinner at Proprietor’s Bar & Table.
55 Miles Biking Nantucket
Days 2 and 3 were all about biking — 55 miles to be exact. I’ve put together a map of each day so you can pick and choose where you want to go.
- Old Mill – Built in 1746, it is the oldest functioning mill in the United States.
- Milestone Overlook Trail – We visited the 400 acres that is locally referred to as Nantucket’s “Serengeti.”
- Sconset Beach / Sconset Bridge / Low Beach Rd – Quaint town with tons of beach.
- Sankaty Head Light – Built in 1850.
- Polpis Harbor / Watts Run – Great place for a swim.
- Windswept Cranberry Bog – Trail with 241 acres of protected land to bike/walk.
- The Wauwinet / Topper’s – Elegant Lunch, Wine Spectator Grand Award Winner.
- American Seasons – Cozy restaurant focusing on Wild Game.
- b-ACK Yard BBQ – Night cap.
- Brant Point Beach – Amazing view of the harbor where ferries come and go. (Plus sick real estate on the walk up.)
- Jetties Beach – Big beach close to town with seaside dining.
- Steps Beach – Shallow, perfectly swimmable beach. Lincoln Rd. has some amazing homes to look at.
- Sanford Farm, Ram Pasture & The Woods – Three trails with 1.7-, 3.1- and 6-mi options.
- Madaket Beach – Popular beach on the far west end of the island.
- Smith Point – Accessible only by four-wheel drive at the end of Madaket.
- Cisco Brewers – Cool spot with a Brewery, Winery & Distillery all in the same place. Food trucks and live music, too if you hit it on the right time/day.
- Greydon House – This inn, restaurant and bar had only been open a couple of weeks when we got there. Cozy, great cocktails, swanky but approachable. Highly recommend ordering a drink at the bar, every detail is perfect.
Additional Towns Visited
Chadd’s Ford, Pennsylvania was a beautiful town with winding roads and original stone houses dating back to the 1700s, rolling hills, and the Brandywine River. Great dining and pubs, like the Four Dog Tavern and The Whip Tavern, out in horse country.
Mystic, Connecticut is home to Mystic Seaport is the nation’s leading maritime museum and one of the premier maritime museums in the world. This was a short stopover, but I would definitely come back and stay overnight. We stopped at the Sea View Snack Bar on the way in to eat a lobster roll at the picnic tables by the water and swung by Mystic Pizza on the way out.
Newport Beach, Rhode Island – The Newport Cliff Walk is considered one of the top attractions in Newport, Rhode Island, in the United States. It is a 3.5-mile public access walkway that borders the shore line. It has been designated a National Recreation Trail. We only made it about 1.3 miles before having to stop due to rain. We will definitely go back and finish another time because the town seemed very cool and the homes were incredible. Like, off the charts mansions that were people’s “summer cottages.”