Southport, Maine: Things to Do, Stay & Eat

Should you stay on Southport or visit from Boothbay Harbor?

Choose Southport for an island stay organized around the property, a beach visit and time beside the water. Choose Boothbay Harbor when harbor departures and village restaurants are the main event. Southport’s bridge-connected island setting suits an inn stay with separate beach and village outings.

A day visit can pair the Hendricks Head area with a meal at Robinson's Wharf. An overnight makes sense when you want the particular inn's rooms, grounds or guest activities to occupy more of the trip. For the wider island outing, use the Southport Island guide; start here to compare the two listed places to stay. For the wider peninsula, compare Boothbay and the access options in the Maine lighthouse guide.

Which Southport inn fits the way you want to spend the day?

At Newagen, the on-site restaurant gives a stay a dining anchor without making every evening a trip back to the harbor. At Ocean Gate, room format changes the stay: its one-bedroom Chickadee and two-bedroom Osprey cottages have full kitchens, while a room is a different arrangement. That makes the cottage choice useful for travelers who want to alternate eating out with cooking. Book the room or cottage category with the kitchen, bedrooms and facilities your group needs. ^2–3

Ocean Gate also advertises kayaks, canoes and paddleboards for guests, plus an outdoor pool and mini golf. Those activities are reasons to leave time at the property. The equipment, pool and mini golf are for inn guests. Choose a water outing suited to the day’s conditions. ⁴

Where can you eat on the island?

Robinson's Wharf is at 20 Hendricks Hill Road on the Southport side of the swing bridge. Its menu includes lobster and other seafood alongside non-seafood dishes and a children's menu, so a group does not have to agree on a lobster dinner. In the October 10, 2026 capture, Robinson’s advertised Friday music in winter and a year-round seafood market. ^5–6

Use Robinson's for the bridge-side meal or a seafood-market stop; consider The Pub when the Newagen property is part of your plan.

Things to do

Hendricks Head has a public beach and a nearby trail managed by Boothbay Region Land Trust.

Hendricks Head combines two separate public outings: the beach, owned and managed by the Town of Southport, and a nearby Boothbay Region Land Trust trail. The woodland route is an easy half-mile loop. Take it when you want a short walk through trees as well as time at the shore; it is not a long coastal hiking route. ¹

Follow Beach Road to the beach area. The land trust places the trail on the right and the parking and beach on the left as you arrive. Keep that distinction when choosing where to go first. Pair the public beach with the land trust’s woodland loop for two different settings on a short visit.

Getting there and around

Use the street address on each place record. Village names can differ from the municipality, and separate waterfront or island locations should not be treated as the same arrival point.

The Route 27 swing bridge links Southport with the Boothbay peninsula, with no ferry crossing. Robinson’s Wharf is beside the bridge at 20 Hendricks Hill Road; the inns and Hendricks Head area are separate stops. Plan an island stay by its property address.

When to visit

Choose dates against the current operator schedule for the places you plan to use. A listing in this inventory does not establish year-round opening hours.

Choose dates around the inn you want and its guest activities. Newagen’s October 10, 2026 notice named October 11 as its seasonal closing date. Robinson’s winter music and year-round seafood market provide a separate reason for an off-season island visit.

Common questions

How do I choose a place to stay or eat in Southport?

Use the municipal inventory on this page, then open the individual place record for its address, facilities and source links.

Choose Southport for an island inn stay, Hendricks Head beach and a short woodland walk. Newagen offers an on-site restaurant; Ocean Gate offers several room and cottage layouts plus guest water activities. Robinson’s Wharf is beside the swing bridge. Stay in Boothbay Harbor if harbor departures matter more than the island setting.

Compare Newagen for an inn stay with The Pub on site and Ocean Gate for its room and cottage choices and guest activities. Robinson’s Wharf provides a separate bridge-side dining option. Match both the property and the meal to your travel dates.

Sources checked October 10, 2026

1. bbrlt.org — Beach ownership, half-mile trail and approach.
2. newagenseasideinn.com — Cape Newagen, accommodation types, The Pub and seasonal notice.
3. oceangateinn.com — Address, breakfast and cottage layouts.
4. oceangateinn.com — Guest activities.
5. robinsonswharf.com — Bridge location, winter music and year-round seafood market.
6. robinsonswharf.com — Seafood, non-seafood and children's menus.