Caroline & Connor

August 22, 2025 • Harwich, MA
107 Days To Go!

Caroline & Connor

August 22, 2025 • Harwich, MA
107 Days To Go!

Things to Do

Beachcomber in Wellfleet

1120 Cahoon Hollow Rd, Wellfleet, MA 02667, USA
(508) 349-6055

Not only one of the prettiest beaches on cape, but the bar/restaurant has some great beverages (try the Mudslides or a GOOMBAY SMASH) and some great grub.

Website

Land Ho!

38 Main Street and, MA-6A, Orleans, MA 02653, USA
(508) 255-5165

The Land Ho! in Orleans is one of our favorite places on Cape...a classic Cape Cod hang out, with a charm and character all its own. Orleans business signs hang from every available ceiling space.

Downtown Harwichport

Route 28, Harwichport, MA

Harwichport has a great downtown area not too far from Wequassett. Here you can find some great spots like 3 Monkeys for some unique drinks (especially the Dia De Los Muertos), Ember for outdoor seating/live music and fire pit, The Port for some drinks, or Perks Coffee Shop / Beer Garden!

Truro Vineyards

11 Shore Rd, North Truro, MA 02652, USA
(508) 487-6200

Head down to Truro Vineyards to enjoy the beautiful winery and some great wine! Enjoy a wine tasting under their pavilion and take a free guided tour of the vineyard and winery, including their state of the art barrel room.

Blackfish

17 Truro Center Rd, Truro, MA 02666, USA
(508) 349-3399

If you want an amazing meal and want to check out where we got engaged take a trip to Blackfish and you will not regret it! But be sure to make a reservation since they book up fast!

Main Street Chatham

Main Street, Chatham, MA 02633

Main Street in Chatham has a lovely selection of shops, restaurants, bars, and other goodies.

Chatham Squire

487 Main St, Chatham, MA 02633, USA
(508) 945-0945

A staple in Chatham! Great seafood and a great night life scene, but get there early or you'll be in a line down the street.

Sesuit Harbor Cafe

357 Sesuit Neck Rd, Dennis, MA 02638, USA
(508) 385-6134

If you want a lobster roll or one of the most underrated breakfasts on cape this is the place to go. Order at the counter and have a seat overlooking the Sesuit Harbor. This spot is definitely a fan favorite so try to get here before or after peak hours.

Sundae School

606 Main St #28, Harwich Port, MA 02646, USA
(508) 430-2444

For all the ice cream lovers...you have to go! A staple ice cream shop on Cape with home made ice cream!

Nauset Light Beach

780 Ocean View Dr, Eastham, MA 02642, USA

The beaches on the national seashore are simply put: amazing. You can't go wrong with any beach, but a few of our favorites are Cahoon Hollow (home to Wellfleet Beachcomber), Race Point in Provincetown, and Nauset Light Beach. If you rent a house for your stay, make sure you ask about beach parking permits! It's $20 a day to park at any one of the 6 beaches that make up Cape Cod's most eastern coast on the National Seashore which are the most breathtaking beaches on the Cape. Plus, you may even catch sight of a great white!

Cape Cod Rail Trail

3488 Main St, Brewster, MA 02631, USA
(508) 896-3491

The Cape Cod Rail Trail is a paved recreational path that runs from South Dennis through Wellfleet along the abandoned Penn Central Railway. The 26 mile trail is great for biking and travels through beautiful forests, kettle ponds and salt marshes. If you rented a house, you may be lucky enough to have some bikes at your convenience, or you can rent bikes at SO many different locations along the trail.