Things To Do in Deer Isle

Deer Isle, with its network of narrow roads to nowhere, is ideal for rambling. It’s a pleasure to explore by car and is also inviting to travel by bike, although hasty and careening fishermen in pickups can make this unnerving at times. Especially tranquil is the narrow road between the town of Deer Isle and Sunshine to the east. 

Plan to stop and explore coves and inlets along the way. To get here, follow Route 15; south of Deer Isle, turn east toward Stinson Neck, continuing on this scenic byway for about 10 miles over bridges and causeways.

Stonington, at the southern end of Deer Isle, consists of one commercial street that wraps along the harbor’s edge. While B&Bs and boutiques have made inroads here in recent years, it’s still a slightly rough-and-tumble waterfront town with some attractive white-clapboard homes mixed in. The best thing to see here is, well, Main Street and the waterfront behind it (it's pictured above). 

Walk down side streets like Seabreeze Avenue and Atlantic Avenue for a closer look at the town.

The town opera house is home to a very good summer-stock theater company called Opera House Arts; log on to its website for a schedule and other details . The Opera House also hosts art events and first-run Hollywood movies.

Active Pursuits in and around Deer Isle

Peer southward from Stonington, and you’ll see dozens of spruce-studded islands between the mainland and the dark, distant ridges of Isle au Haut. These islands, ringed with salmon-pink granite, are collectively called Merchant’s Row, and they’re invariably ranked by experienced coastal boaters as among the most beautiful in the state. Thanks to these exceptional islands, Stonington is among Maine’s most popular destinations for sea kayaking. Many of the islands are open to day visitors and overnight camping, and one of the Nature Conservancy islands even hosts a flock of sheep. Experienced kayakers should contact the Maine Island Trail Association for more information about paddling here; several of the islands are open only to association members.

Sea Kayak Stonington  (tel. 207/266-2717), which has an office on the corner of Seabreeze Ave and Main Street in Stonington, offers guided kayak tours as well as kayaks for rent. Tours generally launch from the public ramp in town, and they range from a half-day tour ($75) to a full-day 7-hour tour ($145) that weaves out through the islands and includes a stop for a swim or a picnic at an abandoned quarry. Three-hour sunset tours around nearby Crotch Island are popular too ($75). Call to see on what days open group tours are offered; otherwise, you can arrange a private tour, but it costs a good bit more. Rentals frun $65–$85 per day, and at least one person in the group needs chart and compass skills and know basic self-rescue techniques.

Osprey’s Echo (tel. 207/367-2796), which launches from a cove a little north of town, which shares the public ramp, offers similar tours at similar rates. Stonington Paddle (tel. 207/200-4778) is more of a rental outfit, though it will match you with a private guide if you’re interested in that.  Outfitters based outside the region that offer guided overnight kayak trips around Merchant’s Row include the Maine Island Kayak Co. (tel. 207/766-2373) on Peaks Island.

Worth noting: Stonington is one of those Maine fishing villages that hosts big-time lobster-boat racing. (There are also races in Searsport and Rockland.) Stonington’s race usually occurs on a weekend in early July—drop by if you’re in the area. Crowds line the waterfront and piers to cheer on their favorites. You’ll either be amazed or horrified by how quickly one of these diesel-powered workhorses can get up to speed when the captain’s going full throttle.