While we have lots of repeat guests at Simmons Homestead Inn, many guests at our lodging here on Cape Cod are first-timers to the area. If you’ve never been to Cape Cod before, we highly recommend that you plan on staying for at least four or five days to really get the most out of your visit. One of the most common questions these first-time visitors usually ask is what to do and see and the top attractions in the area. Here are a bunch of ideas and reasons why you just have to spend a bunch of days here and come back every single year to see more.

1. Explore the greater Hyannis Area.

Our historic lodging in Cape Cod, Massachusetts is located in the Hyannis Port section of Hyannis, and our town has much to offer visitors. Hyannis itself is in the dead center of the Cape and on the Ocean side. Some of the nicest shops, restaurants, art galleries and more including the Cape Cod Mall are all right here. Head down to the harbor 2 miles away and you’ll find ferry service to Nantucket and Martha’s Vineyard as well as harbor cruises. They Hyannis Whale Watching boat leaves on the Bay side 5 miles from here. The John F. Kennedy Hyannis Museum is another popular attraction in town, and for anyone fascinated by the life of President Kennedy, this is definitely a must-see excursion.There is also a Maritime Museum right on the Harbor as well as several great restaurants.

The Cape Cod Central Railroad is another fun attraction and starts right in the center of town. It offers a unique look at Cape Cod. The Coastal Excursion trip takes you through cranberry bogs, past sand dunes and along the Cape Cod Canal. The company also offers a romantic Dinner Train and, during the holidays, you might enjoy either the Thanksgiving Dinner Train or the Polar Express Train Ride.

There are more great restaurants here than anywhere on the Cape. That’s the reason we offer a Wine Hour every night from 5:30-6:30 so we can show you the actual menus of the very best restaurants in town that we recommend. We do not have menus of the others as we want you to enjoy every single minute you are here. We have a handout we have written of exactly what to do around town and a very big map of the Town.

2. Driving the Mid Cape.

The prettiest and most fun part of Cape Cod is the Mid Cape. We have out handout and several maps for heading over to Osterville and then up to Route 6-A all the way out to Orleans and Chatham. 6-A was the original Route 6 and has all the nice local shops, art galleries, potters and antique shops and neat restaurants for lunch or even dinner if you are out there towards evening. Our hand out is constantly updated and each town has it’s own paragraph listing things to see, shops and restaurants and more. The existing Route 6 is like an interstate and should be avoided at all costs 🙂

3. Driving the National Seashore and the Outer Cape.

President Kennedy and his family loved Cape Cod so much so that in 1961, he declared that more than 43,000 acres of Cape Cod be designated as the Cape Cod National Seashore. This acreage actually includes woods and inland areas as well as miles of seashore. The seashore stretches from Nauset Beach all the way to Provincetown at the tip of Cape Cod as well as stretching across the cape to Duck Harbor Beach and points beyond.

You’ll be driving out Route 6, but from Orleans out it is just a 4 lane road and has lots of things to do right off of it.You could a whole day exploring the beaches and attractions located within the Cape Cod National Seashore, which is operated by the National Park Service. Aside from enjoying the beach areas, there are biking, hiking and walking trails, ranger-led tours, lighthouse tours and much more.We have several big maps, our written handouts and booklets of walking trails and the likes. And you can take a dog to any of the beaches except the ares marked off for people swimming. There are a great number of lighthouses along the seashore. Several are open for visitors and most all are open during Maritime Weeks the first parts of May and November.

Right in the middle of the seashore is Wellfleet. It is a nice art community of the Bay Side with lots of shops and local restaurants. On the Bay side they have a dog beach and in town lots of things and shops to see.

Then when you get out to the tip, you’ll hit Provincetown. It is actually where the Pilgrims first landed and was where Captain Gosnold spent a winter early on and named our are Cape Cod. First Winter though the Nauset Indians weren’t overly friendly and they went inland to Plymouth and decided to stay there. There is, however, the huge and tall Pilgrim Monument in the center of town. P’town is a 3 ring circus with lots of funky shops, nice art shops, good food of all kinds and shapes. If you end up there for dinner, you are still less than an hour away for you home here at the Simmons Homestead.

4. Day Trips to Nantucket and Martha’s Vineyard.

Just about everyone seems to love Nantucket and Martha’s Vineyard. Even the ride over on the ferry is fun, and the ferry service in the Hyannis Harbor is just minutes from our lodging in Cape Cod. Some people prefer Nantucket while others sing the praises of Martha’s Vineyard, but truly both offer plenty of beauty and charm. We have a sheet showing what to do and see on each Island and several maps of each.

In Nantucket, you can visit the Nantucket Whaling Museum, which offers an excellent look at the history of whaling in Cape Cod. Nantucket is smaller, so much of the action is concentrated in the historic downtown area, which has been designated a National Historic Landmark District. Lots of shops and restaurants all within a few blocks of the harbor. We’ll give you the names and cellπhone numbers of 2 girls who have vans and take you all over for 2 hours. When you get back to here on the high speed just walk across the street to the Black Cat and have a terrific meal and then the come back and collapse.

Martha’s Vineyard is larger and more residential and offers everything from the oldest carousel in the world to historic lighthouses and much more. One unique offering is the Martha’s Vineyard Camp Meeting Association, in Oak Bluffs which is a National Historic Landmark. This historic site features a mix of beautifully preserved historic cottages that once served as the location for religious camp meetings during the 19th Century.The best town is Edgartown about 6 miles from the dock in Oak Bluff and there are shuttle buses to take you and Tour Buses that wander all over for a couple of hours.

5. The Upper Cape.

The day you leave we will send you down to Falmouth and Woods Hole and then up to Sandwich. We, of course, have maps and our handout to know what to do and see. Sandwich was part of the Plymouth Colony long before the Canal cut through. There is lots to see there from the Sandwich Glass Museum to Heritage Museums & Gardens. Best time at Heritage is late May to early June when 77 acres of rhododendron plants are in every shade of pink and red and white you can imagine. Then if you are heading back towards Boston we’ll run you through Plymouth and visit Plimouth Plantation where there is a reconstruction of what it looked like in the 1640s when the Pilgrims had been there about 20 years.

6. Then After the Cape Cod Trip.

When you get back home and sit around with a glass of wine reminiscing the Cape Trip and looking at the zillion photos you took, you’ll agree that there was so much to see and do that you just have to come back next year ……. and the next and the next.