Chebeague Island Inn Maine Weddings *

by Alicia Forth | Jan 4, 2021 | Wedding

Planning to tie the knot on one of the many islands sprinkled along Maine’s coast? There are a few things you should know. We checked in with Caitlin Prentice, who handles events at two island venues in Casco Bay, Chebeague Island Inn and Diamond’s Edge Restaurant & Marina, for the 411 on weddings off the mainland.

L&L: What are the best opportunities and biggest challenges with island ceremonies?

CP: Best opportunities:

• Beautiful water views that serve as fantastic backdrops and photo opportunities
• Natural settings play a big part in ceremonies – from trees to flowers to birds
• Sunsets
• The ability to step outside the box and create an experience that would not have otherwise been possible if you were restricted to the boundaries of an indoor building

Challenges:

• Weather – given we’re in Maine, you always need a back-up. Rainy/dreary days still make beautiful weddings if you’re prepared and realistic upfront.
• As for transporting guests, if you’re working with someone experienced, that’s not necessarily a challenge. However, if the couple wants an island wedding, they need to be flexible regarding the time of their wedding, should they choose the public ferry (as it runs on a schedule).
• Depending on the venue and island, food may or may not be a problem. If you choose a venue with a restaurant on-site, you don’t need to worry as the venue will most likely handle the food and has a system in place. If you’re at a venue without a restaurant on-site but there’s one elsewhere on the island, I’d contact them first. The transporting cost will probably be less than coming from the mainland and they are already familiar with the island. If you’re on an island where a mainland caterer is a must, ask for recommendations of caterers familiar to island weddings and they will take care of the transportation issues from their end.
• The majority of the islands in the Casco Bay region have a restriction on amplified noise (DJs, bands, etc.) that starts at 8pm. This is in large part due to the fact that sound carries on the water and there are private residents nearby. Sometimes it’s a deterrent for the couple, and sometimes the couple understands and are willing to sacrifice an “all night party” for picturesque views and settings. There may be an indoor alternative for “the late night party.”

L&L:  What do couples most often overlook when planning an island wedding? Do island events require more lead time?

CP: Couples most often initially overlook the cost of barging (aka transporting via ferry for large items) wedding supplies to the island/venue when developing their budget. Depending on the venue, there may be more or less items to barge over (some venues may have a tent, tables, chairs, etc., while others may not). Another oversight tends to be bathrooms, believe it or not. Some island wedding venues may have bathrooms for use, but others may not, in which case porta pottys need to be rented, which are also a bit of an expense. Island events don’t require any more lead time than mainland events. Just like on the mainland, it depends on the venue the couple selects and what the venue provides v. what the couple is responsible for. An island wedding can be planned in 3 weeks, 3 months or 3 years. It all depends on the availability of the venue and the vendors.

L&L: Can you offer any advice for couples about finding vendors experienced with island weddings?

CP:  Ask the event coordinator at the venue – I’m sure he/she knows best. There’s a good chance he/she has a list (written or to memory) of people he/she has worked with in the past and whose product he/she trusts – I know I do. Aside from that, I’d ask the vendor if they have ever worked a wedding on an island and, regardless of their answer, would definitely connect the vendor with the venue person if the couple is not using a wedding planner.

L&L: What transportation options are available?

CP: There are several transportation options for island weddings – the most common being the public ferry, which, depending on where the wedding is, would be Casco Bay Lines. For the wedding party, if they want to arrive separately, I’d advise taking a water taxi. It’s the fastest, most direct way to get to an island. Depending on budget and the size of the wedding, there are a number of companies that can charter a boat. Sometimes, if people are local, private boats are an option for a few guests, but definitely not for transporting the masses. If guests are staying on the mainland and are not in walking distance of the Portland piers, I’d recommend securing a bus or trolley. It’s fun and relatively reasonable in price.

L&L: Please share with us a memorable wedding or two your venues have hosted. What great food, decor or other ideas have you seen that reflect the island locale?

CP: A groom’s family from Tennessee, who had never encountered a whole lobster before, had the unique experience of having Chebeague’s oldest lobsterman, Dick Dyer, demonstrate how to eat a lobster tableside. Being the charmer he is, Dick continued around the table assisting anyone who needed help. All the while, his thick accent and funny anecdotes could be heard through the space — a memorable experience for all in his presence. A couple from San Francisco wanted to take full advantage of Chebeague Island Inn’s Casco Bay location. For their rehearsal dinner, 80 people boarded a private charter to enjoy a cocktail cruise and a spectacular sunset. They cruised a short distance to a field on the Coast of Freeport, unloaded at a private pier and enjoyed a lobster bake under a blanket of Christmas lights overlooking the ocean. On their invitations, a beautiful map of Casco Bay was laid out with their ferry routes and images of lobsters and other ocean critters as demarcations of each location’s event.

L&L: How many weddings do each of your venues host each year?

CP: At the Chebeague Island Inn, we accept a limited number of weddings each summer (last two weekends in May, first two in June, last two in September, first two in October; in addition to one in July and one in August on a first-come, first-serve basis); typically we have around six weddings each season. Chebeague Island Inn is perched on a hilltop overlooking Casco Bay to the west and provides a destination wedding with the simple elegance of a coastal Maine experience and can accommodate up to 250 guests under a tent overlooking the bay. Weddings at the Inn are completely customized, down to the creation of the dinner menu – created by the bride, groom and chef. When you have your wedding at the Inn, you have full use of the entire property for the full weekend.

The restaurant remains open to the public, but only wedding guests occupy the rooms. Lawn games are a popular activity, as are fresh lemonade and iced tea stands. As this is our first season operating Diamond’s Edge, I can’t speak for previous years and trends, but as of now, we have five weddings booked, with new inquiries coming in daily, and we have the capability to host 20 weddings each summer. Diamond’s Edge offers two distinct wedding venues – an art gallery and a tent site. The art gallery, once a wagon shed, has been restored and reinvented and now showcases rotating Maine artwork. It’s a rustic yet elegant, intimate venue for parties of up to 65 people. The tent site is adjacent to a freshwater pond and is separated from the ocean by only a few steps.

It has a sweeping lawn, perfect for cocktails and hors d’oeuvres, a picturesque white gazebo surrounded by flowers and a 46×105 foot Sperry tent that can accommodate 218 guests. It’s one of the few locations in the Maine capable of hosting events of up to 500 people. Our average wedding size for this coming summer is 100 guests. Many of the dinners are lobster bakes. Fun Fact: Diamond’s Edge served as a military base to defend Casco Bay at the time of the Spanish-American War and was known as Fort McKinley. The buildings were constructed between 1891 and 1907 and remained in active use until the end of WWII in 1945. Today, the original buildings remain in place – the former Quartermaster’s storehouse is now the restaurant and the wagon shed is now the art gallery – and are all listed in the National Register of Historic Places.

Planning to tie the knot on one of the many islands sprinkled along Maine’s coast? There are a few things you should know. We checked in with Caitlin Prentice, who handles events at two island venues in Casco Bay, Chebeague Island Inn and Diamond’s Edge Restaurant & Marina, for the 411 on weddings off the mainland.

L&L: What are the best opportunities and biggest challenges with island ceremonies?

CP: Best opportunities:

• Beautiful water views that serve as fantastic backdrops and photo opportunities
• Natural settings play a big part in ceremonies – from trees to flowers to birds
• Sunsets
• The ability to step outside the box and create an experience that would not have otherwise been possible if you were restricted to the boundaries of an indoor building

Challenges:

• Weather – given we’re in Maine, you always need a back-up. Rainy/dreary days still make beautiful weddings if you’re prepared and realistic upfront.
• As for transporting guests, if you’re working with someone experienced, that’s not necessarily a challenge. However, if the couple wants an island wedding, they need to be flexible regarding the time of their wedding, should they choose the public ferry (as it runs on a schedule).
• Depending on the venue and island, food may or may not be a problem. If you choose a venue with a restaurant on-site, you don’t need to worry as the venue will most likely handle the food and has a system in place. If you’re at a venue without a restaurant on-site but there’s one elsewhere on the island, I’d contact them first. The transporting cost will probably be less than coming from the mainland and they are already familiar with the island. If you’re on an island where a mainland caterer is a must, ask for recommendations of caterers familiar to island weddings and they will take care of the transportation issues from their end.
• The majority of the islands in the Casco Bay region have a restriction on amplified noise (DJs, bands, etc.) that starts at 8pm. This is in large part due to the fact that sound carries on the water and there are private residents nearby. Sometimes it’s a deterrent for the couple, and sometimes the couple understands and are willing to sacrifice an “all night party” for picturesque views and settings. There may be an indoor alternative for “the late night party.”

L&L:  What do couples most often overlook when planning an island wedding? Do island events require more lead time?

CP: Couples most often initially overlook the cost of barging (aka transporting via ferry for large items) wedding supplies to the island/venue when developing their budget. Depending on the venue, there may be more or less items to barge over (some venues may have a tent, tables, chairs, etc., while others may not). Another oversight tends to be bathrooms, believe it or not. Some island wedding venues may have bathrooms for use, but others may not, in which case porta pottys need to be rented, which are also a bit of an expense. Island events don’t require any more lead time than mainland events. Just like on the mainland, it depends on the venue the couple selects and what the venue provides v. what the couple is responsible for. An island wedding can be planned in 3 weeks, 3 months or 3 years. It all depends on the availability of the venue and the vendors.

L&L: Can you offer any advice for couples about finding vendors experienced with island weddings?

CP:  Ask the event coordinator at the venue – I’m sure he/she knows best. There’s a good chance he/she has a list (written or to memory) of people he/she has worked with in the past and whose product he/she trusts – I know I do. Aside from that, I’d ask the vendor if they have ever worked a wedding on an island and, regardless of their answer, would definitely connect the vendor with the venue person if the couple is not using a wedding planner.

L&L: What transportation options are available?

CP: There are several transportation options for island weddings – the most common being the public ferry, which, depending on where the wedding is, would be Casco Bay Lines. For the wedding party, if they want to arrive separately, I’d advise taking a water taxi. It’s the fastest, most direct way to get to an island. Depending on budget and the size of the wedding, there are a number of companies that can charter a boat. Sometimes, if people are local, private boats are an option for a few guests, but definitely not for transporting the masses. If guests are staying on the mainland and are not in walking distance of the Portland piers, I’d recommend securing a bus or trolley. It’s fun and relatively reasonable in price.

L&L: Please share with us a memorable wedding or two your venues have hosted. What great food, decor or other ideas have you seen that reflect the island locale?

CP: A groom’s family from Tennessee, who had never encountered a whole lobster before, had the unique experience of having Chebeague’s oldest lobsterman, Dick Dyer, demonstrate how to eat a lobster tableside. Being the charmer he is, Dick continued around the table assisting anyone who needed help. All the while, his thick accent and funny anecdotes could be heard through the space — a memorable experience for all in his presence. A couple from San Francisco wanted to take full advantage of Chebeague Island Inn’s Casco Bay location. For their rehearsal dinner, 80 people boarded a private charter to enjoy a cocktail cruise and a spectacular sunset. They cruised a short distance to a field on the Coast of Freeport, unloaded at a private pier and enjoyed a lobster bake under a blanket of Christmas lights overlooking the ocean. On their invitations, a beautiful map of Casco Bay was laid out with their ferry routes and images of lobsters and other ocean critters as demarcations of each location’s event.

L&L: How many weddings do each of your venues host each year?

CP: At the Chebeague Island Inn, we accept a limited number of weddings each summer (last two weekends in May, first two in June, last two in September, first two in October; in addition to one in July and one in August on a first-come, first-serve basis); typically we have around six weddings each season. Chebeague Island Inn is perched on a hilltop overlooking Casco Bay to the west and provides a destination wedding with the simple elegance of a coastal Maine experience and can accommodate up to 250 guests under a tent overlooking the bay. Weddings at the Inn are completely customized, down to the creation of the dinner menu – created by the bride, groom and chef. When you have your wedding at the Inn, you have full use of the entire property for the full weekend.

The restaurant remains open to the public, but only wedding guests occupy the rooms. Lawn games are a popular activity, as are fresh lemonade and iced tea stands. As this is our first season operating Diamond’s Edge, I can’t speak for previous years and trends, but as of now, we have five weddings booked, with new inquiries coming in daily, and we have the capability to host 20 weddings each summer. Diamond’s Edge offers two distinct wedding venues – an art gallery and a tent site. The art gallery, once a wagon shed, has been restored and reinvented and now showcases rotating Maine artwork. It’s a rustic yet elegant, intimate venue for parties of up to 65 people. The tent site is adjacent to a freshwater pond and is separated from the ocean by only a few steps.

It has a sweeping lawn, perfect for cocktails and hors d’oeuvres, a picturesque white gazebo surrounded by flowers and a 46×105 foot Sperry tent that can accommodate 218 guests. It’s one of the few locations in the Maine capable of hosting events of up to 500 people. Our average wedding size for this coming summer is 100 guests. Many of the dinners are lobster bakes. Fun Fact: Diamond’s Edge served as a military base to defend Casco Bay at the time of the Spanish-American War and was known as Fort McKinley. The buildings were constructed between 1891 and 1907 and remained in active use until the end of WWII in 1945. Today, the original buildings remain in place – the former Quartermaster’s storehouse is now the restaurant and the wagon shed is now the art gallery – and are all listed in the National Register of Historic Places.